Fiction and the Identity of the Boss

The influence of TV and film on the identity of the modern boss is undeniable. Bosses are portrayed on-screen in countless different ways within our favourite TV shows and films that reflect the way we see them both positively and negatively in our daily lives. Whilst writers, directors and actors often draw upon their own personal experiences to represent how managers act in organizational life, these portrayals also feedback in to how these managers themselves construct their identities in the workplace. Bosses might do this in a range of ways by consciously or unconsciously embracing behaviours of certain fictional bosses. They might, for instance, channel Mad Men’s uber-cool Don Draper or gradually realise that they are acting like The Office’s painfully un-self-aware David Brent. They might embody the iron maiden characteristics of The Devil Wears Prada’s Miranda Priestly or the reckless hedonism of The Wolf of Wall Street’s Jordan Belfort. Bosses are, it seems, shaped and sometimes guided by fiction through the cultural and social expectations of how they are supposed to act (and not act), and how they supposed to be (and not be) in the workplace, in what amounts to an ongoing internal battle between how bosses want to be seen – the fantasy – and how they are seen, the reality. 

In a new book chapter written with my colleague and friend Professor Mark Learmonth we continue our exploration of fictional portrayals of bosses (or managers) in popular culture and consider how these shape our understanding of the modern manager. The chapter appears in The Oxford Handbook of Identities in Organizations edited by Professor Andrew Brown (Bath University) and was published by Oxford University Press in January 2020. The book is a tour de force exploration of the issue of identities in organizations containing 55 chapters exploring all manner of issues from career identities to performed identities, fake identities to Trumpian identities and perhaps most importantly, encouraging scholars in this field further to ask: what questions should we be exploring in the coming years to really understand the nature of identity in the workplace? Our chapter, “Fiction and the Identity of the Manager” (pg. 455-470),  has the following abstract that will hopefully pique your interest to read further:

This chapter explores fictional portrayals of managers in popular culture and considers the different ways that they shape our understanding of the identities of managers. Focusing on films and novels, the chapter begins by exploring the fundamental nature of the claim that well-known fiction has a capacity to shape and influence the world, albeit indirectly, and in unobtrusive, relatively unnoticed ways. The chapter builds upon established traditions of literary-orientated work in organization studies to show how fiction can transmit ideals, identity models, and patterns for sensemaking about organizations. However, the chapter also represents a fresh direction for research, focusing on the tensions and continuities across a wide range of contrasting fictional portrayals of manager-like figures. The chapter explores ‘positive’, ‘negative’, and ‘tragic’ portrayals of managers in fictional works to consider how they might help shape who we think of when we consider a ‘manager’ in contemporary society. In doing so, the authors encourage a wider consideration of the cultural content and context of managerial identity work and the ways that it can be imagined and understood.

So, within our work we argue that there is an eternal loop between the fact and fiction of management practice. There is always an element of fact in the fiction within its portrayal (in TV and film or comics or elsewhere) but conversely there is always an element of fiction in the fact of management identity work. These two elements feed one another in an ongoing cultivation of social and cultural understanding of what it is to be a manager. In writing the chapter, Mark and I have discussed countless different bosses in fiction. However, it was only possible to include a handful of these. As there are so many wonderfully portrayed bosses in TV and Film I thought it would be fun to use this blog to explore the whole range of characterisations and consider the wider social and cultural portrayal of the “boss” broadly conceived.

After several nights of brainstorming, I ended up with one hundred of my favourite fictional bosses from TV and film. I then tried to consider the similarities between these characterisations that might explain how we have culturally understood the different sides of managerial identity. I asked: What is the driving force for each of these bosses? What do many of these individual bosses have in common? I then divided the managers up in to categories of managerial identity. These categories are by no means final for any future research but have instead been placed here tentatively to provoke debate (about the types of category that exist but also perhaps more contentiously about who belongs where!). There are ten of these categories in total:

  • The Psychopathic Boss
  • The Mean Boss
  • The Incompetent Boss
  • The Rule-driven Boss
  • The Greedy Boss
  • The Renegade Boss
  • The Burdened Boss
  • The Heroic Boss
  • The Predatory Boss
  • The Good Boss

It is, of course, possible for a boss to be predatory and a psychopath, rule-driven and incompetent but I placed them where it seemed the film or TV show’s writer was suggesting the boss’s core drive could be found. In what follows I have arranged the images of these bosses in to ten collages so that this can be played as a “Bosses from Fiction Quiz”. A companion to our chapter that could be used for teaching (to question our own cultural assumptions about managerial identity) or just for one’s own amusement. See how many of the films and bosses you recognise: one point for the film and another point for the name of the character of the boss in the film. To be clear, “bosses” here in this blog applies broadly. It can range from a CEO to a convenience store manager, but also playfully includes the odd mafia boss and other ‘managers’ that have clearly been shaped by our understanding of those in charge, overseers, head-honchos and so forth. 

So…to begin with the type of boss you probably want the very least:

Identity One: The Psychopathic Boss 

One of the most common and well-known management identities portrayed on screen is that of the psychopath. These individuals manage narcissistically, amorally, and solely in pursuit of their own aims and goals. They are more than willing to leave you dead in a ditch, just as long as they hit their targets, maximise profits and get their own way. There is evidence that one in five CEOs displays psychopathic tendencies (which seems quite low!), and that psychopaths in leading roles are three times more likely than in the overall population. There is a whole body of literature that explores this dark side of management theory, claiming that organizational psychopaths and the implications of their existence (in the workplace needs to be taken much more seriously. The 2003 Joel Bakan’s documentary The Corporation even went as far as claiming that the modern corporation (if analysed as a person) displays all the behavioural elements and characteristics of a psychopath (“callous unconcern for the feelings of others”, “incapacity to experience guilt”). In turn, the corporation is the perfect breeding ground for psychopathic behaviours and individuals most aptly able to show little regard for the feelings or well-being of others somewhat inevitably rise to the top. 

Here are ten examples of psychopathic bosses from TV and film – click on the collage (see how many you know!) and then read on to explore more about them. 

1. Gordon Gekko (Wall Street, 1987) 

“We make the rules, pal. The news, war, peace, famine, upheaval, the price per paper clip. We pick that rabbit out of the hat while everybody sits out there wondering how the hell we did it. Now you’re not naive enough to think we’re living in a democracy, are you buddy? It’s the free market. And you’re a part of it. You’ve got that killer instinct. Stick around pal, I’ve still got a lot to teach you.”

In the modern era of films no character has personified the psychopathic businessman as closely as Gordon Gekko. The now infamous “greed is good” speech has become synonymous with 80s neoliberal excess in which, fairly or unfairly, managers of finance of the time were portrayed as entirely amoral individuals purely interested in accumulating wealth. In the film Gekko (played by Michael Douglas) mentors a young, up-and-coming stockbroker Bud (played by Charlie Sheen) teaching him the ins-and-outs of insider trading to manipulate and buy up stock to turn large profits – often at great expense for the companies and the jobs of the people who work within them. Gekko does so callously and without remorse, at one stage when being asked why he had to wreck a company he responds “Because its wreckable, that’s why!” However, if Oliver Stone’s film was meant as a scathing critique of these kind of soulless, corrupt, financial practices, its audiences had other things in mind. Douglas himself has professed great surprise that so many people see Gordon Gekko not as the villain but as a hero. Speaking in an interview in 2018 he said: “It’s always shocked me how many people on Wall Street say to me, you’re the reason I became a stockbroker.” Interestingly Douglas also goes on to say that he adopted elements of behaviour of several real life Wall Street bosses to create the character of Gordon Gekko, reflecting this loop between fact and fiction. It seems a great irony that this psychopathic manager has had such a large cultural influence, but for all the wrong reasons. Rather than act as a cautionary tale it (along with many other factors!) fed in to a cultural celebration of psychopathic behaviour in the corporate world, so that by the early 21stcentury we had financial districts full to the brim with wannabe-Gordon Gekkos – what on earth could possibly go wrong? 

2. Stromboli (Pinocchio, 1940) 

“You will make lots of money…for me! And when you are growing too old, you will make good…firewood!”  

Disney have a great track record over the years of producing the most despicable and easy-to-hate villains. From the evil queen in its original feature Snow White and the Seven Dwarves to Scar in The Lion King, the writers and animators have a knack for bringing pure evil to life on screen for our amusement. Stromboli, the psychotic theatre director and puppeteer in Pinocchio, is perhaps one of the most under-appreciated in its classic canon. The monstrous Stromboli exploits the naïve wooden boy, putting him on stage to make his fortune and caging him when he isn’t working. He makes no bones about his willingness to kill Pinocchio once he has served his purpose. In more recent years the Romany depiction of the character has been considered as potentially racist, drawing on a caricature of Gypsys as child snatchers, deceptive and money hungry. Pinocchio eventually escapes the wild clutches of Stromboli, but not before the mad theatre director cements his place in the history of wonderfully depicted psychotic managers. 

3. Blake (Glengarry Glen Ross, 1992) 

“Let’s talk about something important. Put. That coffee. Down. Coffee’s for closers only. You think I’m fucking with you? I am not fucking with you. I’m here from downtown. I’m here from Mitch and Murray. And I’m here on a mission of mercy. Your name’s Levine? You call yourself a salesman, you son of a bitch?

When David Mamet’s play Glengarry Glen Ross came to the big screen, it not only gave us the best ensemble cast a cinephile could hope for (Jack Lemmon, Al Pacino, Kevin Spacey et al), it also gave us one of the most horrible bosses imaginable. The film – a black comedy/thriller – centres around a group of salesman who have been given one night to sell highly undesirable real estate to a highly disinterested set of leads. Blake  – an executive sent from head office (played by Alec Baldwin) – delivers the news to the group of salesman in a blistering speech which (after humiliating them all) concludes with the line: “first prize is a Cadillac Eldorado. Anybody wanna see second prize? Second prize is a set of steak knives. Third prize is, you’re fired.” This stark reality created by Blake leads the salesman to go to extraordinary measures in an attempt to keep their jobs with quite disastrous consequences. The play and subsequent film was inspired by Mamet’s own experiences in a sales office and the management tactics employed whilst he himself struggled to adapt to life as a salesman. Famously, the film has so many expletives in it that the cast referred to it as “Death of a Fucking Salesman” – I suspect anybody who has worked in such an environment will understand entirely. 

4. Christian Deville (Corporate, 2018) 

“Now, we all know there is no God, but there is, a tonne of money to be made in his name”

Christian Deville (played by Lance Reddick) is one of the most recent examples of managers to appear on this list. Set within a multinational corporation Hampton Deville, this brutal satire of corporate life follows the experiences of the oppressed workforce and their psychopathic CEO. It is told through the eyes of the junior executives who have to experience this horrible boss on a day to day basis and the tactics they employ to cope with him and their awful working conditions. In crafting the character of Deville Reddick went as far as to research real-life CEOs and their psychopathic tendencies. In a recent article he says: “I don’t know that in terms of personality type, he’s that different from real CEOs of multinational corporations. There’s a certain personality type, there’s a certain level of megalomania. I don’t know that you necessarily see yourself as right all the time, but you think your vision is the right vision. It’s almost like it’s God-given in your mind.” The manager portrayed here is entirely amoral and nihilistic, and reflects the dark and frightening attitude of the kind of manager who has no desire to please anyone but himself. In one hilarious scene, we witness Deville ask his employees to “look to your left, now look to your right…one hundred percent of these people are ruining my fucking day”. This need to dominate and humiliate seems to be central to the psychopathic identity so that people remain obedient and completely in line. 

5. Patrick Bateman (American Psycho, 2000)  

“I have all the characteristics of a human being: blood, flesh, skin, hair; but not a single, clear, identifiable emotion, except greed and disgust. Something horrible is happening inside of me and I don’t know why. My nightly bloodlust has overflown into my days. I feel lethal, on the verge of frenzy. I think my mask of sanity is about to slip”

The intentional blurring of fantasy and reality is one of the most fascinating elements of the fictional portrayals of managers. We not only see what managers might do on screen but also see what we imagine they might want to do with all rules and constraints removed. Brett Easton-Ellis’s 1991 novel American Psycho introduces us to Patrick Bateman, vice-president of investment banking corporation, and cleverly plays with the shallow, vacuous reality of yuppy 80s lifestyle and the murderous, insane thoughts, fantasies and actions(?) of its main protagonist. On the release of the novel, American Psycho (which contains a scene in which a young woman is nail-gunned to the floor and raped with the aid of a hollow tube and a rodent – yes, it is that shocking!), there was outrage. Many women’s groups called for a ban and some books stores refused to even stock it. Interestingly, the film of the same name (released in 2000) confounded critics even further by enlisting a female director, Mary Harron, who (through the stellar acting of Christian Bale) brought out the darkly comic aspects of the character which Ellis was originally aiming for whilst not shying away from the psychopathic actions of the lead character. In one famous scene Bateman bludgeons his co-worker to death in his living room shortly after asking him: “Do you like Phil Collins?” and proceeding to play Sussudio rather loudly to drown out noise (and because…well, who doesn’t love that particular Phil Collins track?!). 

Another interesting aspect of this film picked up in a New York Times article, is Bateman’s borderline obsession with one Donald Trump, merely a businessman at the time. He has a copy of Trump’s book The Art of the Deal on his book shelf and laments Trump not being invited to a party that they were due to attend. The irony of Bateman idolising a man who would famously go on to say he could “stand in the middle of fifth Avenue and shoot somebody” and “not lose any voters” is now even more stark. Without becoming overtly political you wonder whether one American psycho influenced another and then filtered back in to the brash and brazen actions of the other again later – that interesting loop between fact and fiction that seems ever present in these managerial identity constructions. One question that many fans of the book and the film have posed, however, was just how much of the actions of Bateman were reality and how many were constructions of his fantasies – lots of hints (in the book especially) were given about the fantasy world of Bateman making you question what was “real”. However, Harron and Ellis have suggested that while some of the psychopathic aspects of Bateman were in his head, certainly not all of them were and the former sees it as a “failure” on her part to properly convey this in the film. In terms of the ongoing controversy surrounding the book – and to a lesser extent the film – Ellis has become frustrated over the years with people’s inability to separate him from his character. In an article from The New York Times in 1991 he sardonically said: “I would think most Americans learn in junior high to differentiate between the writer and the character he is writing about. People seem to insist I’m a monster. But Bateman is the monster. I am not on the side of that creep.” This points to a strange inability to separate artist and creation – a bizarre bleeding of fantasy with reality both within and outside of the original source. 

6. Dick Jones (Robocop, 1987)  

“I remember when I was a young executive for this company. I used to call the old man funny names – Iron Butt, Boner… once I even called him… Asshole – but there was always respect. I always knew where the line was drawn, and you just stepped over it, buddy-boy. You’ve insulted me and you’ve insulted this company with that bastard creation of yours. I had a guaranteed military sale with ED 209 – renovation program, spare parts for twenty-five years… Who cares if it worked or not?”

Dick Jones (the senior president of Omni Consumer Products) is yet another fantastic on-screen representation of the ruthless and amoral corporate boss. We find Jones (played by Ronny Cox) in a dystopian future in which corporate interests have come to dominate the police force and how they pursue justice – through the implementation of highly experimental cyborg technology. Jones is more than happy to use criminal means (including murder) to ruthlessly pursue profit and only eventually gets his comeuppance at the hands of “Robocop” who is protecting other workers. Quite fittingly Jones is shot numerous times in the boardroom, sending the evil president crashing through the office window plummeting to his death, much to the relief of his subordinates. 

7. Cruella de Vil (101 Dalmatians, 1956)  

“Congratulations. You’ve just won gold, silver, and bronze in the Morons Olympics! Shut up! My business, my reputation, my life, has been ruined because you three incompetent twits let yourselves be outsmarted by a bunch of dumb animals! And you call yourselves men? Huh? I’ve seen more intelligent pieces of carpet!”

While Cruella de Vil is perhaps the most famous (and feared!) of all Disney villains, you might not conventionally consider her a boss. And yet, throughout the film as she attempts to find, catch and skin the 101 Dalmatians for a new fur coat, she is repeatedly referred to as “boss” by her dimwit henchmen. As the quote above wonderfully captures, she  – like the worst bosses we will encounter here – hurls all manner of insults at these guys as they fail to live up to her expectations. Originally appearing in Dodie Smith’s 1956 Novel of the same name, Cruella was brought to life by Disney on screen and was modelled in part on Bette Davis in the 1950 classic All About Eve (albeit slightly less beautiful and a lot more demonic). Within the film, Cruella is depicted by Disney animator Marc Davis  as skeletal, constantly smoking and a domineering figure. In an interview, Davis claimed she was based in part on “one woman [he] knew who was just a monster. She was tall and thin and just talked constantly – she knew what she was saying, but you couldn’t get a word in edgewise.” Whilst she was a pretty nasty character anyway, her real downfall was her obsession with her one true love, fur: “I live for furs, I worship furs. After all, is there a woman in all this wretched world who doesn’t?” The fact she is willing to skin the newly born puppies to achieve this end, and destroy anybody who gets in her way, certainly earns her a place in the list of psychopathic bosses. 

8. Daniel Plainview (There Will be Blood, 2007) 

“I have a competition in me. I want no one else to succeed. I hate most people…. Well, if it’s in me, it’s in you. There are times when I… I look at people and I see nothing worth liking. I want to earn enough money I can get away from everyone.” 

In 2007 the writer-director Paul Thomas Anderson delivered a film, There Will be Blood, that not only ranks regularly in the lists of best films of the 21st century, but also introduced one of the most memorable characters of recent times. The film follows the life of oil tycoon, Daniel Plainview (played by Daniel Day Lewis), and his efforts to get a small town to allow him to drill for oil during the late 19th and early 20th century. It is loosely based on the 1927 novel Oil! by Upton Sinclair although Anderson has always been clear that he used the novel as a starting point (the first hundred pages), drawing inspiration from real-life tycoon Edward Doheny (on which Sinclair’s work was based) but then diverging greatly thereafter. Anderson explores the emergence of ruthless capitalist men like Plainview as they burst on to the scene during the California oil boom to manipulate and dominate completely unprepared frontier people and their communities. The film wonderfully explores the relationship between Plainview and the local preacher, Eli Sunday, showing how the bloody minded and unrelenting nature of capitalism (as personified within Plainview) was prepared to do anything it takes to make money from the situation. The concluding scene of the film in which a confused and petrified Eli Sunday listens to Plainview explain how he has completely and utterly outsmarted him by drilling a pipe under his land (“I drink your milkshake…”), culminates in one of the most violent scenes in modern American film history. 

In an interview in 2007 Day-Lewis explained why he found the character of Plainview compelling enough to play and cited his desire to understand people he otherwise would not: “I suppose that has always appealed to me, and I am always most often intrigued by lives that seem very removed from my own. With Plainview it wasn’t the violence of the man or the misanthrope of the man that attracted me particularly, but just that unknown life in its entirety.’ We too spend the entire film trying to understand what drives this man to wish to dominate and exploit (to threaten his rivals with cutting their throats in the night), and by the end we are left with the brutal truth – to succeed, to win and to demonstrate exactly who is in charge. 

9. Lex Luther (Superman, 1978)  

“You were great in your day, Superman. But it just stand to reason, when it came time to cash in your chips, this old…diseased…maniac…would be your banker” 

The character of Lex Luther dates back to 1940 through his original appearance in DC’s Action Comics as the arch-nemesis of Superman. In the original creation, by Jerry Siegel and Joe Shuster, he was depicted as a mad scientist (with his own full head of red hair!) and with very little relation to the high powered business man, owner of LexCorp many of us have come to know today (in the comics, films or TV shows like Smallville). In many respects (especially when it comes to superheroes) we can best understand a character’s identity by understanding their arch nemesis. There is a fantastic quote in the 2004 Quentin Tarantino film Kill Bill vol. 2 which explores Superman’s identity that is worth reading at this point (or watching it if you want the full experience):

Superman didn’t become Superman. Superman was born Superman. When Superman wakes up in the morning, he’s Superman. His alter ego is Clark Kent. His outfit with the big red “S”, that’s the blanket he was wrapped in as a baby when the Kents found him. Those are his clothes. What Kent wears – the glasses, the business suit – that’s the costume. That’s the costume Superman wears to blend in with us. Clark Kent is how Superman views us. And what are the characteristics of Clark Kent. He’s weak… he’s unsure of himself… he’s a coward. Clark Kent is Superman’s critique on the whole human race.”

If we follow this understanding of Clark Kent/Superman’s identity crisis, we can also view Lex Luthor as a critique of the human race as well. It is Lex who is a powerful and very well respected business man, hiding his pursuit of retail estate and global domination behind philanthropic acts. It was during this period (the late seventies/early eighties – Superman 2 followed shortly after in 1980) that we witnessed the increasing power of CEOs within multinational corporations, challenging the dominance of national governance. Luthor (played by Gene Hackman) in the film is portrayed even more so as a CEO than in any other previous incarnation of this character. He explains how his father taught him “son, stocks may rise and fall, utilities and transportation may collapse. People are no damn good, but they will always need land and they’ll pay through the nose to get it!” The need for Luthor to destroy Superman – the only real force for good standing in his way, capable of stopping him – is essential if he is to extend his business interests and accumulate greater wealth and power.

10. Sam Stone (Ruthless People, 1986) 

“A bad salesman will automatically drop his price. Bad salesmen make me sick”

The 1986 film Ruthless People contains one of the largest ensemble of despicable and unlikeable people ever put to film. Sam Stone (played by Danny DeVito), undoubtedly the worst of these people, is the owner and manager of a clothing manufacturing firm. He despises his wife Barbara (played by Bette Midler) who he only married as he thought her father (a filthy rich CEO) was at death’s door. The father unexpectedly hung on for fifteen years leaving Stone at the end of his tether. When the father finally pops his clogs, Stone devises a plan to kill Barbara and receive the inheritance all to himself but not before she is  kidnapped and held for ransom – a ransom that Stone will obviously never pay. The story twists and turns around Stone’s intentions and frustrations in collecting his fortune by hook or by crook in what is in this case an extremely comedic portrayal of a psychopathic manager (for those of you who aren’t too easily offended, here is how Stone answers his telephone to wrong numbers in his office). In his own defence, however, Stone spends much of his time blaming others for his own despicable actions. Of Barbara, his long-suffering but equally terrible wife, he says: ”Let’s face it – she’s not Mother Teresa. Gandhi would have strangled her.” While he is a light-hearted portrayal of a ruthless bastard of a manager, Stone is a great example of how a psychopathic boss need not always be incredibly successful (as most of the aforementioned ones are) – they can be hilariously bad at what they do as well. 

Identity Two: The Mean Boss

Related to psychopathic bosses, but not nearly as bad, are mean bosses. These individuals might not be willing to kill you to achieve their goals – they still retain some form of moral compass – but they are quite happy to make life a living hell for any subordinate not willing to fall in to line. This form of management identity has been popularised and legitimised over the past couple of decades through numerous reality TV shows. Individuals such as Gordon Ramsay (in Hell’s Kitchen [2005] and Ramsay’s Kitchen Nightmares [2007]) epitomise the mean-spirited boss who uses fairly extreme methods including shouting in subordinates faces and brutal character assassination to force people to bend to his will. This persona adopted by Ramsay (which can be seen in all of its glory here) is built directly from this widespread cultural understanding and acceptance of the manager as a bullying, hectoring, rude figure that must keep his or her otherwise lazy employees working hard or they will fail to deliver the required results for the organization. It is, for all intents and purposes Locke’s Theory X (the idea that workers are inherently lazy and require robust and forthright management) brought to life on screen – sometimes through parody, sometimes through social criticism and occasionally through outright appreciation of their methods. Here are a few of my favourite examples of mean bosses in action:

 11. Katherine Parker (Working Girl, 1988)  

“Why that little slut! That goddamn little…bitch! Secretary!”

Katherine Walker (played by Signourney Weaver) is a financial executive at the top of her game – she is smart, intelligent (speaks fluent German) and is not short on self-confidence (“I am, after all….me”). Mike Nichol’s Working Girl introduced us to this character in the late 80s when things like the gender pay gap were not even on the agenda and women at the top of corporations was even more rare than it is today. The film centres around the relationship between Parker and her new ditsy, unpolished secretary Tess McGill (played by Melanie Griffiths), who is on her final warning after finding it impossible to get on with previous managers. McGill looks up to the hard-working, hard-nosed boss and when Parker breaks her leg on a skiing trip she does all she can to imitate her and try to step up in to her shoes and do a better job (in the hope of taking her bosses job – and even her man played by Harrison Ford). According to one recent article about Working Girl, When Weaver let her female Wall Street friends read the script, they asked, “This awful secretary steals your man, wears your clothes, takes your office – who’s going to sympathize with her?” A very good point. The only way Nichols can make this dynamic work is by making Parker absolutely awful in as many ways as possible – rude, abrasive, unlikeable etc so terrible in contrast to the lightness of her secretary that we end up rooting for McGill anyway despite how underhand her approach might be.  

Working Girl has been celebrated many as a feminist film– of “girls” working hard to get to the top. It has also been accused, however, of pitting women against each other in the workplace and of suggesting we can only have one woman at the top of the organization. It might unwittingly encourage female bosses to build an identity around suspicion of younger women, to see them as dangerous interlocutors who might replace them. Indeed, this “older successful woman – young up and coming woman” dynamic is also a strong trope in Disney films – we see the wicked older queen try to kill Snow White, the wicked step-mother go after Cinderella . Other feminist authors criticised Parker on the release of the film suggesting as ‘bright though she is, her success stems from a fragile tissue of privilege and contacts, rather than intelligence or substantive achievement.’ There is a lot to admire in Parker though insofar that she can ‘play the game’, the office politics well enough to rise to the top whilst fending off the hyper-masculine bullshit that comes with the territory. Parker is  a mean boss then, but she works in a mean world in which she has probably always needed to be mean. One imagines that someday (in a scenario after the film’s end) she would probably return to the top in some way or another – as she says herself, “never burn bridges. Today’s junior prick, tomorrow’s senior partner.”

12. Miranda Priestly (The Devil wears Prada, 2000) 

“Details of your incompetence do not interest me.”

Miranda Priestly, head of influential fashion magazine Runway, is a character that first found life in Lauren Weisberger’s 2003 novel The Devil wears Prada. Weisberger had worked as a personal assistant in the fashion industry and this semi-fictional novel followed the demeaning and embarrassing treatment she had received before leaving, not least by her boss. Priestly has many similarities with Katherine Parker (explored at number 11 on our list) but whilst being hugely successful and sure of herself she is infinitely more rude (a compilation of her most savage moments is well worth a watch). The film essentially follows Andy – a new female recruit to the magazine and the savage ways in which Priestly and many other colleagues abuse and ridicule her despite her best efforts and intentions. (NB: the film is supposed to be a comedy, but is unintentionally a lot more dark than it intended to be).   It has long-been rumoured that Miranda Priestly was based on Variety magazine Editor Anna Wintour (Weisberger worked for Wintour, who apparently has a notorious temper and ruthless attitude with her staff). Indeed, Meryl Streep and Wintour once met over tea to discuss the role and other things they had in common. However, more recent reports – from an interview with co-star Emily Blunt – suggest Streep actually based the character on somebody entirely different. Blunt says: ‘Meryl didn’t actually base it on Anna Wintour—well, she told Anna that,’ Emily explained. ‘She based it on two men in Hollywood that she knew – who will remain nameless, but I know who they are.’ 

The film goes out of its way at times to portray Priestly as being completely without warmth as a manager – so much so that any trace of humanity in the boss was deleted from the final cut of the film. In one deleted scene, for example, we see her drunk husband causing an argument at a party and subsequently mouthing “thank you” to Andy who diffused the bad situation with rather quick thinking. When the scene  was released it was rather shocking to see this vulnerable and softer side to Priestly, that the film had gone out of its way to erase. It left me feeling that including these kinds of scenes might add greater dimensions to female characters of this kind and that while this is standard fare for many male bosses in films (we regularly see male anti-heroes), it is seen much less within women portrayed in Hollywood films. Identity as we all know is incredibly complex and a man or a woman can be a complete bastard in the morning, and an angel over lunch. Portraying identity as so consistent within films without depth and even hypocrisy merely misleads people in to assuming that individuals only have one side to their workplace identity, that what we see is what everyone else gets. This, as far as I can tell, makes bullying and abuse in the workplace all the more easy to get away with. 

13. Montgomery Burns (The Simpsons, 1989) 

“Family, religion, friendship. These are the three demons you must slay if you wish to succeed in business.” “The man has no idea how to behave like a billionaire. Where’s the dignity? Where’s the contempt for the common man?”

Montgomery Burns (or Mr. Burns to most of us) is a creation of Matt Groening and voiced by Harry Shearer in the long running animated TV show, The Simpsons.  Burns, as owner and boss of Springfield power plant, takes a lot of his mean-spiritedness out on his unfortunate employees, not least Homer Simpson. Simpson and Burns have a particularly tumultuous relationship with Burns seemingly incapable of even remembering his name. This escalated to such a point of frustration for Homer that he was accused of murdering him in the famous “Who Killed Mr Burns?” episode (mirroring the famous “Who shot JR?” storyline found in Dallas surrounding the death of another evil tycoon). Burns has done a whole host of other terrible things down the years from stealing oil found under the elementary school, sexually harassing Marge, attempting to kidnap dogs to make a new tuxedo (in a superb scene in which he channels Cruella De Vil) and blocking the sun out over Springfield to force citizens to pay for his power plant produced electricity rather than switching to solar. 

Groening has suggested the character is based upon his old high school teacher, Mr Bailey and the 20th Century magnate J.D. Rockefellar. In modern times, Mr Burns has become a cultural icon of sorts that executives are compared to if they are considered as particularly heartless and money grabbing. Media mogul Rupert Murdoch for instance has been compared to Burns in recent years – an unfair comparison on the hilarious Burns if ever there was one.   

14. Malcolm Tucker (The Thick of It, 2005)  

“Who was it that did your media training, Myra Hindley? It’s terrible! All these hands all over the place. You were like a sweaty octopus trying to unhook a bra. It was like watching John Leslie at work.”

Of all the characters written about here, the boss with the funniest and most ferocious things to say is undoubtedly Malcolm Tucker. Creation of Armando Ianucci for the political satire/sitcom The Thick of It, Tucker (played by Peter Capaldi) is director of communications for the political party in government (and later out of government). He rules with an iron-fist ensuring that ministers and their special advisors adhere to party policy and where necessary to his guidance to minimise explosive political fall outs. Inevitably things go wrong, and Tucker is not shy in telling people exactly what he thinks of them (for a particularly foul-mouthed, but hilarious example, watch this). In a 2009 Guardian article, Capaldi says: “The thing that amuses me about [Tucker] is he thinks he’s incredibly powerful and clever – and he is very clever and he does suss things out quickly – but he’s sort of an evil clown.” The basis of the character has always been assumed to be the Labour director of communications Alistair Campbell, who had a similar reputation for keeping people in line with an acerbic tongue. Campbell himself has since suggested after watching The Thick of It, that the comparison with Tucker ‘never rang true’ , and that it was at times rather frustrating: ‘[people] seemed to want me to accept that the reason I didn’t like it was that the portrayal was too close to home. On the contrary, I didn’t like it because it was so far removed from the motives of most of the people I know.’ Capaldi himself has admitted that numerous influences (including Campbell’s colleague Peter Mandelson) probably had just as much, if not more, influence of the development of his interpretation. 

The joy of satirical portrayals of managers, however, is gained through exaggeration and perhaps this is just another example of that. We sometimes need to inject a little bit more than exists in real life to bring out the small nuggets of truth and, of course, to make them more fun to watch.  With that in mind, here are five especially brutal put downs by Tucker that (if you have ever seen The Thick of It, you can’t help but hear in Malcolm’s deep Scottish accent: 

“He’s useless. He’s absolutely useless. He’s as useless as a marzipan dildo.”

“The guy is an epic fuck-up. He’s so dense that light bends around him.”

“No offence, but you’re not leadership material, yeah? I mean, fucking curtain material in that outfit but, you know.”

“You’re so back-bench, you’ve actually fucking fallen off. You’re out by the fucking bins where I put you.”

“When I need your advice, I’ll give you the special signal: which would be me being sectioned under the fucking mental health act.”

Never change Malcolm. Never change. 

15. Park Dong-ik (Parasite, 2019) 

*describing the smell of an employee* “Like an old radish. No. You know when you boil a rag? It smells like that.” 

When Boon Joon-Ho’s Parasite was awarded best film at the 2020 Oscars, the greatest surprise was not that such an incredible film had won. The greatest surprise was that Oscar voters – famous for sticking with the obvious, white, male dominated/American films – had shocked everyone by actually picking the best film, and a foreign language film at that. In the film we encounter a dirt-poor family of conmen (and women) who one-by-one slowly infiltrate themselves in to a wealthy families suburban home largely through lies (the son as piano teacher, the mother as cleaner, the daughter as art-therapist, the father as driver, they extend slowly like a virus through the house). Park Dong-Ik, an incredibly busy CEO of a tech firm, is the man of the house and the film wonderfully explores the developing relationship between him and his new driver, who has virtually no experience of driving for a living but manages to carry off the role without being detected. In one scene, we see the family (who aren’t known to be a family by the Parks) rehearsing scenes at their own home in an effort to play them out later to manipulate and get more out of their clueless employers. The Independent called the film “an intricate examination of class conflict”. And whilst it can be enjoyed purely as a farcical dark comedy, it can also on a different level be viewed as a searing social satire not only of Korean life but of life between the haves and the have-nots, the upstairs and the downstairs. In doing so, the film turns the relationship between bosses like Park Dong-Ik and the “help” on its head and then in a surprise twist ending, hammers home why being humiliated and talked-down to can lead people to shocking and quite desperate measures. 

16. Mike Baldwin (Coronation Street, 1960) 

“You screw this deal up and you’ll never clean a lavatory in this town again.”

Mike Baldwin is one of the first managerial characters I can remember witnessing as a young child. My mother watched Coronation Street religiously (and still does) and I can still recall this nasty boss of the clothing factory threatening his machinist staff with the sack if they dared do anything wrong or cross him and his business plans. After thirty years in the role (and thousands of episodes) Baldwin (played by Johnny Briggs) eventually succumbed to old age and hospitalisation due to pneumonia, staggering back to his business and eventually dying of a heart attack on the factory floor. Grace Dent wrote in The Guardian that ‘Mike was like [Coronation Street’s] King Lear, broken and confused, wandering through a storm, berating his family who he believed had stolen his kingdom.’ Baldwin (and all mean managers) could perhaps take a lesson from Bill and Ted’s Totally Bogus Journey: “You might be a king or a little street sweeper, but sooner or later you dance with the grim reaper”. 

17. Buddy Ackerman (Swimming with Sharks, 1994) 

“Look I can appreciate this. I was young too, I felt just like you. Hated authority, hated all my bosses, thought they were full of shit. Look, it’s like they say, if you’re not a rebel by the age of 20, you got no heart, but if you haven’t turned establishment by 30, you’ve got no brains. Because there are no story-book romances, no fairy-tale endings. So before your un out and change the world, ask yourself, “what do you really want?” 

This is the first time that Kevin Spacey appears on this list, but it is certainly not the last. If you were to pick one actor who captures and characterises the multifaceted nature of managerial identity on-screen over multiple roles and multiple years he would be at the top of the list. Buddy Ackerman is possibly the least well-known but the best example of how power can shift within manager – subordinate relationships. Buddy is the vice president of production for a major film studio. He is akin to a Weinstein type figure (Bob not Harvey) – all-powerful, he expects his every need to be catered to by his underlings at the snap of his fingers. In his review of the film renowned critic Roger Ebert suggests “Ackerman is a first-class, gold plated egotistical monster, the kind of man whose morning greeting is likely to be, “shut up! Listen! Learn!” The film is particularly interesting in that it follows the gradual emergence of Guy as he learns to challenge Buddy and ultimately replace him, by becoming just as egotistical and just as horrible in nature. In one brilliant scene(with Buddy tied bloody and beaten to a chair) Guy screams about how unfair Buddy’s behaviour has been towards him. Buddy says if anyone really wants to be the “top dog” in this industry you have to go through what he has and those before him – you have to swim with sharks – “you have to take it, you have to make it yours”. The main message of the film being that to make it in this world of management, juniors experience horrible bosses and in turn become horrible bosses themselves. Often those who appear to be most horrible are often merely hiding behind a false front that is only too easy to be seen stripped away over time, leaving a shadow of the man that once exists. Embarking on a career in management can in this sense have massive costs to a human being in a variety of ways.   

18. Hunter, (Storks, 2012)  

Hunter: “Junior, you know why I built my office entirely out of glass even though birds can’t see glass?”  

Junior: I do not.” [birds fly smack into the glass]  

Hunter: “Power move!”

The film Storks revolves around the hilarious idea that once the storks stopped delivering babies to expectant mothers and fathers, they required a new way of making a living. In order to do so they switched their business in to a postal delivery service instead, streamlining and becoming a worldwide brand as Cornerstone delivery service. Hunter is the CEO of Cornerstone and the villain of the piece. He is portrayed as a typical greedy, corporate manager who tries to recruit the hero of the film, Junior, in to doing his bidding and following in his footsteps to become “Bossss!” (which is said by Hunter in a long deep tone, signifying that it is essentially the pinnacle of human achievement). Management here is seen as dominating employees, trying to have them fired and doing all you can to increase stock prices to secure promotion. Storks is another in a long line of modern animated films that ultimately sees corporate greed (and the ruthless CEOs in charge) beaten and replaced with a more wholesome, inclusive and fair set of organizational practices (see also Cloudy with a Chance of Meatballs, The Lorax, Big Hero 6 and many others). 

19. Yubaba (Spirited Away, 1999) 

“Anyone can see that you’re a lazy, spoiled, crybaby and you have no manners. This is a high-class place I’m running here. So there’s no job for you – now get out! I’ve got all the lazy bums I need.”

Hayao Miyazaki, the legendary Japanese animation director and founder of Studio Ghibli, is celebrated today for creating strong female characters. He once said: “Many of my movies have strong female leads – brave, self-sufficient girls that don’t think twice about fighting for what they believe with all their heart. They’ll need a friend, or a supporter, but never a saviour. Any woman is just as capable of being a hero as any man.” He has been hailed from numerous quarters as a feminist director. While fans of Studio Ghibli might think of the great heroes of his films being female (Sen, the young hero girl from Spirited Away being a prime example), he has also created a range of fantastic female characters who can be considered villains. The 1999 Miyazaki film Spirited Away provides us with perhaps the strongest example of this in Yubaba, the owner and manager of a magical bathhouse for spirits and demons. A young girl, Sen, gets lost in this magical world (think Alice in Wonderland) and has to beg Yubaba for a job to try and earn her way out of the world and back to her parents. In a wonderful scene, Sen’s mouth is literally zipped up by Yubaba who is desperate not to hire this young girl, but eventually has to relent as she is cursed to hire anyone who asks for a job. Some viewers have connected themes within the film (having to give up her name, work for free) to child trafficking and human slavery, and Yubaba’s place within this as ringleader and dominator in chief. 

However, another perspective is that the film is a coming-of-age drama of learning to enter a world of work that seems dangerous, but within which Sen thrives albeit with the threats and manipulations of Yubaba. Either way, the film is regularly ranked the greatest animated film of all time, and the worker-manager interplay between Sen and Yubaba – between the powerful and the seemingly powerless is a huge part of the reason for this success. Her experience within (and ultimate escape from) this dangerous but exciting world of work (showing that she can be a key member of a team) is another step towards becoming a woman. As Sen sits safely back in her car with her parents at the end of the film on the way to her new house, we hear her say that everything’s going to be okay. It is perhaps a less common message found within films that tough experiences (in workplaces, and with bad managers) can sometimes bring out the best in us in order to rise above them. 

20. Bob Kelso (Scrubs, 2001)  

“Listen up, Interns! Notice the definition in the upper calf. (Lifts pant leg to reveal his oddly youthful legs) Look at it, damnit! See that. Back in ‘Nam the choppers used to hover about eight feet over my head and I’d jump in. You should have seen the look on Charlie’s face. (To Rex) Not the enemy, son. The pilot, Charlie-horse. Great guy. He didn’t make it back. Where’s the cake?”

Bob Kelso (played by Ken Jenkins) is chief medical officer at Sacred Heart hospital in the long running TV sitcom Scrubs. He gains most of his satisfaction from being as mean as humanly possible to the younger doctors, and appearing as if he couldn’t give a damn about any of them. As with many depictions of managers with a mean streak, in later seasons we learn that appearances can be deceptive and he actually cares an awful lot about his staff, his patients and the job in general. One interesting reoccurring theme within depictions of managerial identity is the way that it often portrayed as layered – a mean boss can also privately be a burdened boss who uses put-downs and comedy to hide their own insecurities and fears. 

21. Les Grossman (Tropic Thunder, 2008)

Less Grossman: “I couldn’t have done it without you”

Studio Executive Rob Slolom: “Really?”

Les Grossman: “No, dickhead. Of course I could. A nut-less monkey could do your job. Now, go get drunk and take credit at all the parties”

When  Tom Cruise read the script for Ben Stiller’s 2008 film Tropic Thunder he agreed to appear in the film on one condition: that he could create a new character in it, that he felt was essential for the plot to work. Cruise suggested that the film really needed a “greedy pig studio executive who really represents the gross part of Hollywood”, and so Les Grossman was born. The film was subsequently a smash-hit and Cruise’s disgusting, dancing, “fat fingered” executive became the most talked about character in the film (Cruise was asked to repeat various scenes on TV for months afterwards). The plot of the film revolves around a group of actors who are unknowingly dropped in to the middle of an actual war zone to make a film seem more realistic. Driven by the outrageous demands of Grossman – who wants a more extreme depiction more likely to win during awards season – the director and actors go to extreme lengths to make the film executives happy. There has never been any official confirmation on who Grossman is based on, but every sign points to that of Harvey Weinstein. Cruise knew Weinstein and never hid his disgust for the film executive, even before the horrific revelations of rape and sexual assault that were later learnt. He had an horrific temper and many of the mannerisms and demands of Grossman can now be directly read about in the pages of brilliant books like Jodi Kantor and Megan Twohey’s She Said and Ronan Farrow’s Catch and Kill. So it seems like the dark side of Hollywood (in this case the bullying and manipulation of studio executives) was being explored on camera way before the #metoo era, through apparently fictional portrayals that had more than a whiff of truth about them. 

22. Chief Bogo (Zootopia, 2016) 

“Now, I’m going to open this door and you’re going to tell that otter you’re a former meter maid with delusions of grandeur who will not be taking the case!”

The plot of Disney’s Zootopia (inexplicably renamed Zootropolis for UK audiences), revolves around a scenario in which animals have evolved to leave their carnivorous desires behind to get all get along in perfect harmony – lions and tigers work side by side with gazelles and deer (and different types of animals) in various jobs and industries. The hero of the film is Judy Hopps, a young bunny rabbit who aspires to be the first ever graduate from Zootopia police academy. Against all the odds she achieves this, only to be allocated as a meter maid (parking warden for UK readers), by her abusive boss Chief Bogo. Bogo is horrifically mean towards Judy, continuously telling her that she simply isn’t up to the job of real police work. The film has been lauded for being the first Disney animation to really address overt sexism in the workplace but it also uses divisions between animals as an exploration of racism as well – although many suggest it falls short at adequately exploring the latter. Breaking with tradition in Disney films (where the protagonist usually eventually flees a horrible boss), this film teaches young girls to see things through and prove themselves in working roles, albeit without actively rebelling or speaking out against oppressive managerial behaviour. 

Identity Three: The Incompetent Boss

A large proportion of managerial identities are ones that the individual is entirely, or at least in part, conscious of possessing. For instance, Malcolm Tucker or Miranda Priestly know that they are mean – indeed, they utilise it as part of their identity for their own advantage.  Other identities however, are developed externally without the possessors knowledge and are largely due to a significant lack of self-awareness. One such identity, that has significant social influence through TV and Film, is that of the incompetent manager. Managers are held up as figures to be laughed at because they simply cannot see what the rest of us can see – they are ridiculous, hapless figures, incapable of properly organizing the workforce. Within the management discipline, the “Peter principle” probably best encapsulates this managerial identity. The “Peter principle” is the idea that an employee rises through an organizational hierarchy to their level of incompetence. That is, they are promoted based upon their success in previous positions and they continue with their progression until they no longer possess the required skill or knowledge to remain competent. There are numerous articles about how to cope with incompetent managers of this kind (including “understand the incompetence”…easier said, than done!). Unfortunately, most people reading this blog will have experienced an incompetent manager of this kind more than once over their career so far. And these managers tend to be so memorable because they make for the funniest anecdotes and of course the funniest of TV and film characters. 

See how many of these men – incapable bosses in TV and film do tend to be men! – are familiar to you in this collage of incompetent bosses:

23. David Brent (The Office, 2001) 

“I can wake up one morning and go, ‘I don’t feel like working today. Can I stay in bed?’ ‘You’d better ask the boss.’ ‘David, can I stay in bed?’ ‘Yes, David.’ Both me. Not me in bed with another bloke called David.” 

Few depictions of managerial identity have had such a widespread cultural influence in Britain than David Brent in Ricky Gervais’s cult TV series, The Office. The program was one of the first to successfully bring the mockumentary style to the small screen (following in the footsteps of great films such as This is Spinal Tap), it is a fly-on-the-wall look at life inside the office of a small company in Slough called Wernham Hogg. We meet David Brent, a self-described “chilled-out entertainer” who is not only completely incompetent but tries to be best friends with his workforce with cringe worthy attempts at humour, many of them completely inappropriate whilst also trying (and failing) to be painfully politically correct. He is also dazzlingly un-self-aware to the extent that he makes awful mis-judgments of language, tone and timing. In one famous scene, he informs his staff that news has come from head office that some people within the office have to be made redundant: “Well, there’s good news and bad news” Brent says. “The bad news is that Neil will be taking over both branches, and some of you will lose your jobs. Those of you who are kept on will have to relocate to Swindon, if you wanna stay. I know, gutting. On a more positive note, the good news is, I’ve been promoted. So, every cloud…you’re still thinking about the bad news, aren’t you?” Gervais revealed in one interview that the inspiration for Brent came from multiple managers he had over the years but the first was during an interview for a job: “His opening sentence was, “‘I don’t give shitty jobs’; I just looked at him and nodded. He said, ‘If a good guy comes to me,’ (he pointed at me to let me know he already knew I was a good guy), ‘and says I wanna work hard because I wanna better myself, then I will make that happen.” Gervais explained that the boss then phoned a friend at some point regarding his job and said “Yes of course he’s 18’; then he winked at me and did the Pinocchio nose mime. (It was nothing to do with fork lift truck driving but it was for work in a warehouse). I never saw him again, but I used to do impressions of him as I told the anecdote over the years. He was the very first Brent I can remember. There have been many since.”

The show is a difficult watch at times because of just how realistic it is – we have all met multiple David Brents. Men who think they are god’s gift to the world whilst in reality being completely useless. There is a peculiarity about Brent though that despite all of this Gervais makes you care about the man. You regularly see glimmers of humanity and a realisation that he is in fact out of his depth and not the man that he wishes that he was. This is so painful to watch at times that the show still has a relatively small committed fanbase. Many people still tell me that they simply cannot watch more than five minutes of the show because it is so cringe-inducingly realistic. This is a testament to the writing but also the reason for its wider cultural relevance (most people who haven’t seen the show will still understand a reference to their boss being like David Brent). Gervais accurately captures the incompetence, fragility and insecurity of the middle manager in a way that very few other people have managed to before or since. 

24. Gordon Brittis (The Brittis Empire, 1991) 

“Since I have been manager, I am proud to say there have only been twenty-three deaths. And not one of them was a staff member.”

The Brittis Empire – starring Chris Barrie as hapless leisure centre boss Gordon Brittis – first aired in 1991. It follows the chaotic attempts of Mr Brittis to manage Whitbury Leisure Centre with hilarious and somewhat farcical results. He is well-meaning in all of his actions (as many managers are) but can never seem to get anything right. Despite this, everything always seems to work out anyway and his workforce emerges unscathed. In many respects a pre-cursor to David Brent (with many similar traits – incompetence and a complete lack of self-awareness) Brittis is another archetypal example of the perceived uselessness of many bosses. Rather than being considered the answer to organizational problems they are commonly viewed as the cause of them and the reason why problems get worse. 

25. Kenny Daly (Frasier, 1993)  

“Yeah, the station manager’s sort of the head honcho. You know, the go-to guy. You could replace virtually everybody at the station except for me. [he notices Roz behind him] And Roz.”

Kenny Daly (played by Tom McGowan) played a small but memorable role in TV’s multi-Emmy award winning sitcom Frasier. Daly is the radio station manager where Frasier delivers his show and whilst he attempts to be a hard-nosed, no-nonsense manager, he is simply incapable of showing the level of ruthlessness necessary to do this. In short, Daly’s incompetence comes from the fact that he is simply too nice to ever be an effective boss in this kind of environment. On one occasion Kenny tries to stamp his authority in the radio station by firing Frasier only to back down a few hours later because he feels so bad. He subsequently goes to the owner of the station and ends up getting fired himself. This characterisation nicely highlights that to be a good manager you sometimes have to be a bastard – and not everyone is cut out to be that. 

26. Basil Fawlty (Fawlty Towers, 1975)

“We have a Spanish porter at the moment, he’s from Barcelona. It’d be quicker to train an *ape*!”

The British have a peculiar knack for creating characters that are both wholly incompetent but inherently loveable in their actions. Horrible on the surface but relatable and sympathetic on some deeper level. Fawlty Towers is regularly voted the greatest ever British sitcom and much of this is down to the lead character and owner/boss of the hotel, Basil Fawlty (played by John Cleese, who also created the series with Connie Booth). Fawlty acted as if the guests in the hotel were there to make his life difficult and treated them accordingly. In one famous scene a guest asked if anywhere serves French food. Fawlty replied: “Yes, France, I believe. They seem to like it there. And the swim would certainly sharpen your appetite. You’d better hurry, the tide leaves in six minutes.” Donald Sinclair, owner of Gleneagles hotel in Torquay, is now widely known to be the inspiration for Basil Fawlty in which Cleese and his fellow Monty Python co-stars regularly stayed. In a 2018 interview Cleese spoke hilariously about his various encounters with Sinclair where he captures the hoteliers approach to management as: “I could run this hotel properly if it wasn’t for the guests.” He recounts watching Sinclair sitting staring in to space once within the hotel, and as soon as the manager saw a guest approaching he would quickly busy himself pretending to be doing work. And then when the guests approached him he would pretend not to notice them until they actively interrupted him. In another bizarre encounter Cleese talks about a time where Eric Idle left his bag behind the hotel desk. When he went to retrieve it from Sinclair, the mad cap manager explained that it wasn’t behind the desk anymore, it was in the garden behind a wall. When Idle enquired why, Sinclair said that he had reason to believe there might be a bomb in the bag so he had taken the precautionary measure to take it outside. This kind of bizarre behaviour inspired Cleese to bring this character to life on screen as Basil Fawlty, and over the course of just twelve 30-minute episodes, the world was introduced to the most wildly incompetent manager to ever grace our screens. The crescendo of chaos within the show was reached in a now infamous scene where Fawlty – exasperated with everything going wrong around him – gives his broken down car a “damn good thrashing!” Fawlty is a fantastic portrayal of how awful managers are often willing to blame anyone or anything but themselves in an organizational setting. 

27. Frank Cross (Scrooged, 1988)  

James Cross: You know what they say about people who treat other people bad on the way up?” 

Frank Cross: Yeah, you get to treat ’em bad on the way back down too. It’s great, you get two chances to rough ’em up.”

Charles Dickens’ 1843 novella A Christmas Carol has had dozens of TV and film adaptations over the years. Whereas most of these remained faithful to the original plot and characters, one film sought to re-imagine the classic tale in a modern setting. Instead of Ebenezer Scrooge we get Frank Cross (played by Bill Murray), a miserly TV executive who is largely inspired by writers’ Mitch Glazer and Michael O’ Donaghue’s own experiences with TV executives throughout their careers. Like Scrooge Cross is visited by three ghosts – unlike Scrooge however this includes a violent fairy who isn’t afraid of giving Cross a taste of his own medicine. The immortal line “the bitch hit me with a toaster!” possibly isn’t what Dickens had in mind but against all odds this holiday classic holds up as one of the funniest and heart-warming adaptations of the text. Cross, who has spent much of his life and career being awful towards his employees, is taught a lesson throughout the film, making him reconsider his awful ways. One of the core messages of the film is that being an incompetent manager (at one point telling an employee to staple antlers on to a mouse’s head!) can come from simply not caring about your job or your life in general. As with Scrooge, we come to understand the historical reasons for Cross’s miserable behaviour and he in turn learns to manage instead with “a little love in his heart”. 

28. Bobby Pellitt (Horrible Bosses, 2011)  

Bobby Pellitt: “You’re three hours late. What’s the deal?” 

Kurt Buckman: “I was at your father’s funeral.” 

Pellitt: “Uh huh. Well, maybe that excuse would have flown when my dad was here, but I’m in charge now.”

The fact that a Hollywood franchise has been created from the societal dislike of bosses just reflects how ingrained it is across Western culture. In the first instalment of Horrible Bosses we meet three employees who have simply had enough of their downright awful bosses (but can’t for whatever reason afford to leave their current positions). They therefore agree to kill each other’s bosses (decreasing the likelihood of being caught) so that they will be free from working for such awful people. I will explore all three managers by the end of the list but the first of these is CEO of Pellitt & Son, Bobby Pellitt (played by Colin Farrell). This “horrible boss” is a cocaine addicted nightmare that missed his own father’s funeral so that he could finally start to call the shots at the company he has now inherited. In an interview about his portrayal of the character, Farrell explains “[Pellett] thinks he’s god’s gift to everything…but he’s really not, he’s sad and pathetic and lonely”. The screenplay was written by Mark Markowitz who based the horrible bosses on his own experiences down the years in various offices. Markowitz recalls taking a day of annual leave and finding many of his possessions had been removed from his desk by his boss and stacked Jenga-like with a post-it note attached stating “No personal items in the desks”. This kind of petty, awful behaviour to an employee beggars belief at times and one might think that a lot of these sorts of actions stem from a huge amount of insecurity and of wanting to stamp authority but in doing so looking absolutely ridiculous. In one interview, the director of the film Seth Gordon said of Markowitz “I’m grateful that he suffered, because he wrote a great script!”

29. John Williamson (Glengarry, Glen Ross, 1992)

“You’ve got a big mouth…now I’m gonna show you an even bigger one”

I have already explored David Mamet’s fantastic play turned film in entry number three of this blog. There I explored one of the head honchos of Mitch and Murray – Blake – an alpha-male played by Alec Baldwin who commanded and demanded respect. Whilst being a total bastard he was obviously also quite successful at what he did. John Williamson (played by Kevin Spacey) can be considered none of these things. He is a spineless, brown-nosing middle-manager and is there within the organization (the sales office) to hand out leads to the sales men and, at least in theory, is supposed to make the sales men’s lives easier so that they shift more real estate. Unfortunately, Williamson’s general incompetence contributes to Ricky Roma (Al Pacino) missing out on a sizeable bonus (six thousand dollars and a Cadillac). In one scenewe see Roma absolutely tear in to Williamson asking him: “whoever told you that you could work with men?” before delivering possibly the withering and well-delivered put down in film history, looking at his beleaguered manager with a mix of contempt and pity, whilst uttering “you child”. This captures the way that managers can so often be seen as getting in the way of “real work” and that managerial identity, especially in sales arenas, is intertwined with a macho-culture that can be absolutely devastating if you aren’t up to the task. 

30. Michael Scott (The Office, 2005) 

The most sacred thing I do is care and provide for my workers, my family. I give them money. I give them food. Not directly, but through the money. I heal them. Today, I am in charge of picking a great new health care plan. Right? That’s what this is all about. Does that make me their doctor? Um, yes, in a way. Yeah, like a specialist.”

Since it debuted in 2001 Ricky Gervais’s The Office has been sold to over 80 countries around the world ranging from India to Germany. All of them differ to some degree from the source material but it seems that the idea of an unknowingly incompetent, arrogant boss is a universal theme. Undoubtedly the most successful adaptation thus far has been the American version which turned David Brent in to Michael Scott (played by Steve Carrell), a similar but subtly different characterisation. In a 2011 article Gervais explained the reason why Brent needed to be adapted for an American audience in to something slightly different. While Americans tend to applaud ambition and success British are more comfortable with failure and therefore life’s losers: Failure and disappoint lurk around every corner. This is due to our upbringing. Americans are brought up to believe they can be the next president of the United States. Brits are told, ‘it won’t happen for you’”. Gervais also highlights British people’s extensive use of irony in everyday life to tease and poke fun at elites to explain why “we had to make a Michael Scott a slightly, nicer guy, with a rosier outlook to life. He could still be childish, and insecure, and even a bore, but he couldn’t be too mean.’ This reiterates that whilst there is a universal thread of disdain for managers there are cultural differences in how we display this disdain and how far we are willing to push this. Obviously this, in turn, shapes how managers construct their own identities – how much they are able to get away with in their particular workplace and why developing a managerial identity in a culture alien to your own can be riven with difficulties. 

Identity Four: The Rule-driven Boss 

Another way we commonly see bosses portrayed is through a hard-nosed commitment to the rules and regulations of organizational life and/or wider capitalist norms. This tends to be the kind of boss who can recite the managerial guidelines verbatim from memory (“Article 4, sub section 3b requires us to do X”) and who is more than willing to sacrifice a more pragmatic solution or an employee’s well-being to stick to agreed rules. In many ways this view of the manager’s role correlates with Max Weber’s description of bureaucratic management in which a rational organization would follow strict and formal rules that would in turn lead to the highest level of efficiency and organizational success. Whilst Weber was optimistic about the logics of bureaucratic management, he was less willing to consider the potential downsides of pursuing such an approach. Fortunately, we had fantastic writers like Charles Dickens and later, makers of TV programmes and Film to explore these somewhat darker sides of being a stickler to the rules in the name of organizational profit. Yet, to this day, it remains an identity which managers gravitate towards, preferring to play things by the book usually in the hope of being recognised as loyal to the hierarchy and worthy of retention, promotion and ultimately as the creator and enforcer of the rules themselves. 

Here is a collage of my favourite rule-driven bosses – any of them look familiar? 

31. President of the Electrosteel Corp, (Modern Times, 1936)  

[from the Telescreen to a worker in the restroom] “Hey! Quit stalling, get back to work! Go on!”

Charlie Chaplin’s Modern Times is not only a classic film of its era, it is also eerily prescient about the future of work. It follows a day in the working life of Chaplin’s nameless “little tramp” character who is newly employed at the the Electrosteel Corporation. We meet the president of the corporation (played by Al Ernesto Garcia) at his desk looking bored, completing a jigsaw puzzle and reading his paper (all whilst his employees are working flat-out to keep up with production speed). Evidently this is not enough, and the manager calls for even greater speed and more production from his poor over-worked staff. Later, we witness the manager trialling a speed-eating machine that will eliminate the lunch hour and experience something akin to CCTV being imagined/invented(!) in the workplace. The president uses a form of closed circuit camera to spot the tramp taking a cigarette break in the bathroom and demands he returns to work immediately. Considering it was only 1936, this kind of technology was not even close to being used within public spaces let alone the workplace, which reflects how ahead of its time this onscreen portrayal is. It was as if Chaplin knew what was coming – and he was trying to warn us of the creeping power of the managerial class and the powerlessness of many of those below them. 

Modern Times is at heart an inciteful critique of industrialization and Taylorist modes of production. It was directly influenced by Chaplin personally witnessing the awful conditions of factories during the great depression. How they controlled people and how work was increasingly impinging on every part of individual’s life. Ultimately, the film is just as relevant today for understanding the controlling nature of managers albeit through ever more technological means. It has long been argued by Marxist scholars that workers treated in this way – as cogs in wheels, rather than as ends in themselves – become  alienated from the end product and become indistinguishable from the machine. Indeed, in the film’s most famous scene Chaplin is sucked inside of the factory machine and slides around the cogs. The little tramp simply is not cut out for factory life and the final scene of the film sees him escaping the factory and walking away down the road with his lady love in to the sunset. It would be the last we ever saw of Chaplin’s tramp on screen – it could even be argued that management killed the silent film star. 

32. Sandra (Compliance, 2012)  

“Ha! Well, I’m just trying to do my job!” 

If you were to hear the pitch for the film Compliance, you would be forgiven for thinking it was a little far-fetched. Sandra (played by Ann Dowd) is boss of the Chickwich fast-food restaurant. She receives a telephone call from a man identifying himself as a police officer who has been in touch with her regional manager about a stolen purse. He tells Sandra he has reason to believe one of her employees (Becky, played by Dreama Walker) stole a purse and subsequently gets her to call the girl to her office to search the employee. The man on the phone gradually gets Sandra to strip search Becky and includes other employees in increasingly degrading acts towards the employee culminating in Becky performing oral sex on one of the employees. Eventually after the dreadful occurrence Sandra ends up contacting the regional manager who says he has no knowledge of any potential theft and that it was all a hoax. Sandra claims that she is an innocent victim and that she herself was just following orders. If all this sounds incredibly rather far-fetched, then it is important to note that Compliance is based on actual events that are now commonly referred to as the strip search phone scam. Over the course of ten years seventy cases were recorded, in which managers were instructed to get their employees to follow orders, many of them degrading and sexually explicit. 

There are other precedents for this kind of behaviour in observed studies, where individuals blindly follow orders of people in authority. The Milgrim experiment or electric shock study and the Stanford prison experiment both showed that if encouraged to by authority figures or directed through institutional rules, a high proportion of individuals will carry out immoral acts that cause harm and distress to others.  Much of this research came through a desire to understand why and how so many people in Nazi Germany were able to comply with orders within concentration camps. Compliance is a film that revolves entirely around a similar attempt to understand the chain of command between managers and subordinates, and their willingness to comply with orders and rules. It highlights the dangers of unreflectively carrying out commands by those we deem to be in charge and encourages a greater level of resistance against managers who we perceive to be carrying out immoral, unethical or just plain criminal acts. 

33. Johnson (Peep Show, 2003) 

“In business, Jeremy, you learn that every man has his price, and I judge yours to be… £530.”

British sitcom Peep Show follows the lives of two thirty-something flatmates (Mark and Jeremy) using a point of view camera system which allows you to see the world through the protagonists eyes. Cameras were often mounted on the actors heads or directly over the shoulder to give the feeling that you were actually experiencing events yourself – making them more emotive and affective. Johnson (played by Paterson Joseph) is Mark’s boss – a senior loan manager – at the firm JLB. He follows what he considers to be the rules of business, regularly quoting business maxims and trying to emulate those in the business world he admires most. He considers the working environment to be Darwinian in character, and as “top-dog” it requires strict adherence to rules, his rules in particular. It requires us to prioritise the company’s needs above all, even beyond romantic relationships. At one point Johnson reaffirms this stance saying: “I mean, does a balance sheet ever come crying and saying that it needs some time to think about things? A business doesn’t say it loves you, then run off with a buddy.” There is in this sense a sort of underlying sadness to this seemingly uber-confident manager. Johnson is ultimately addicted to playing the management ‘game’ and trying to succeed within it because he has very little else in his life and we increasingly see throughout the series how he is masking failures in his life behind the comfort of the rules of business. In this sense, managers can cling to a rule book because it is safe and it gives meaning to their lives rather than serving any other real purpose. 

34. Thomas Wake (The Lighthouse, 2019)  

“And if I tells you to pull up and apart every floorboard and clapboard of this here house and scour them down with your bare, bleeding knuckles, you’ll do it! And if I tells you to yank out every single nail from every moldering nail-hole and suck off every spec of rust till all them nails sparkle like a sperm whale’s pecker, and then carpenter the whole light station back together from scrap, and then, do it all over again, you’ll do it! And by God and by Golly, you’ll do it smiling, lad, cause you’ll like it. You’ll like it because I says you will! Contradict me again, and I’ll dock your wages. You hear me, lad?”

A relationship between a boss and his or her wider team can of course be fraught with difficulties, but at least there is a shared burden between the employees. Humour can be used, blame can be distributed and there is relief that others will have to endure management from time to time. It is usually possible to find a quite area to either get on with work, or avoid it in some way or another. In some situations, however, the worst of situations perhaps, an employee can find themselves in a permanent one-on-one working arrangement with their boss. This can, of course, be fantastic if you get on well with your boss and there is a mutual respect. But where this isn’t the case, it can also be hell on earth. The Lighthouse is a film about such a scenario in which a lighthouse keeper, Thomas Wake (played by Willem Defoe) rules with an iron fist over his younger newly appointed assistant Ephraim Winslow (played by Robert Pattinson). We meet Wilmslow as he encounters Wake for the first time, an alcoholic curmudgeon who instructs him exactly what he is to do within the lighthouse and most importantly what he is not to (never go upstairs to the lamp). The film follows the descent of these two men in to madness as they are marooned together in their cramped living quarters, living on top of each other – literally at times. Eventually Winslow snaps at his manager: ‘you think yet so damned high and mighty cause yer a goddamed lighthouse keeper? Well, you ain’t a captain of no ship and you never was, you ain’t no general, no copper, you ain’t president, and you ain’t my father – and I’m sick of you actin’ like you is!” Eventually, Winslow pays the ultimate price for his inability to stick to Wake’s rules, although the exact cause of his death is shrouded in our own experience of events through the increasingly drunk and manic minds of the two characters. 

The film is inspired by real life events in what is now known as The Smalls Lighthouse Tragedy of 1801. In a tale similar to that of the film, the two lighthouse keepers argued regularly and when the assistant died in an apparent freak accident, his body was stored in the lighthouse by the manager (Thomas Wake) for months as it slowly decomposed. It was only found eventually later once the manager was relieved from duty, and by this time Wake was so mentally and physically scarred by the burden of working around the body for months that he was unrecognisable to his family and friends. As director of the film, Robert Eggers, explains: “The way the story is told and ends is like a folk tale, so how much truth there is to this ‘true’ story, who knows,” he said. “Very little of that story aside from the fact they’re both named Thomas came into The Lighthouse, but the idea that they were both named Thomas struck a chord. I was like, ‘Okay, this is a movie about identity, and can devolve into some weird, obscure places.'” The film wonderfully explores the relationship between a manager and a subordinate and how power can be abused in horrific ways, especially if there are few checks and balances on interpretations of an obscure rule book. Incidentally, in the years following the Smalls lighthouse tragedy, their workplace rules were changed so that three people would be working within the lighthouse at any one time, in order to support one another and ensure guard against loneliness and indeed madness!  

35. Mr Florenz Ziegfeld (Funny Girl, 1968)  

Florenz Ziegfield: “Miss Brice, do I have to remind you this is my theatre?”

Fanny Brice: “So what, nobody argues with the landlord?”

William Wyler’s Funny Girl centres around the life of Fanny Brice, played by the great Barbara Streisand. We watch her rise to fame, through her first auditions, first performances (one of my favourite ever movie scenes), her first loves and, of course, her heartbreaks and glorious return. Fanny dreams of being on stage but ‘doesn’t look like the other girls’ – she is beautiful, but just not conventionally so. One of the most interesting relationships in the film is between that of Fanny and Florenz Ziegfeld based on the real life theatre producer and mogul of the same name who dominated broadway for 25 years at the start of the 20th century. Ziegfeld expects his orders within the theatre to be obeyed at all times by the girls but Fanny is essentially a comedic firebrand who re-writes the rules of what it is to be a leading lady on the stage as one of the famous ‘Ziegfield Follies’. In one brilliant scene Fanny essentially ‘works to rule’ after Ziegfeld demands that she play her part how its written or she be fired. She comes on stage and sings the song (“I am a beautiful reflection of my loves affection”) exactly as written but with an improvised bump in her belly providing a completely different meaning to the song. At first Ziegfeld is furious but realises the crowd adores it and so later backs down and orders her to play it exactly the same way the following night. Fanny Brice’s real life-story that Funny Girl is based upon however suggests she was not quite as rebellious against Ziegfield or his rules. Indeed, in the film Fanny consistently disobeys Ziegfield’s orders, changing routines to suit her comedic talents, but as one account suggests in real life she never actually did these things and if she had of done she would have been instantly dismissed. To a large extent the film, Funny Girl whilst wonderfully entertaining,  is a whitewash of Fanny Brice’s life, but it does contain a fictional portrayal that matched more with the changing attitudes towards women in the workplace starting to emerge in the late nineteen sixties. For this, Streisand was awarded with an Oscar for what is one of the greatest female performances in film. 

36. Bill Lumbergh (Office Space, 1999) 

“Milt, we’re gonna need to go ahead and move you downstairs into storage B. We have some new people coming in, and we need all the space we can get. So if you could just go ahead and pack up your stuff and move it down there, that would be terrific, OK?”

The scene that best captures Mike Judge’s 1999’s Office Space is one in which three office workers gather menacingly around a particularly frustrating printer in a field. To the tune of Geto Boys – Still (Gangster rap for those not in the know) they set about the printer with a baseball bat to smash it to smithereens. The film is a hilarious exploration of the rebellion of the office worker against the frustrations that they face in the daily lives, most notably at the hands of their boss Bill Lumbergh (played by Gary Cole). His favourite phrase “so, what’s happening?” is used repeatedly as a way of checking why workers are not complying with the tight rule book that he has created at the software firm, Initech. This is repeated so regularly that one of the employees has a nightmare of Limburgh semi-naked having sex murmuring “can you get me those TCAP reports ASAP?”. Clearly something has to give. The three workers subsequently decide to team up in an effort to hack in to the bank accounts of the company to steal money and escape their mundane working lives. Many people have suggested that this film (and other similarly timed things like The Office) were such a hit because they captured a cultural wave of disaffection with this kind of mundane office life. How unproductive it was and how it breeds characters like Lumbergh which make people’s lives miserable and cause organizational issues. Indeed, with many people having worked from home for the past three months due to the corona virus lockdown, one wonders if anybody in their right mind would ever want to go back to an office environment. For those that must return, we might expect to see a more battered printers in fields and parking lots in 2021. 

37. Steve (Arthur Christmas, 2011) 

“Who cares about one single child?”

If we were to imagine an alternative universe where Christmas did not exist and Amazon had to invent Christmas time, Steve would be the resulting Santa Claus. Aardman Animations’ 2011 film Arthur Christmas explores the complex process and planning that takes place to deliver presents around the globe each year. It not only gives us an elderly Santa Claus, Malcolm (voiced by Jim Broadbent), who still actually delivers the presents in a high tech sleigh but also his two very different sons, Arthur and Steve, who to varying degrees wish to replace him some day. Steve (voiced by Hugh Laurie) is currently in charge of the huge manufacturing and logistics operation that organizes the making and the delivery of the presents (helped of course, by thousands of elves). Steve is militaristic and expects everybody to fall in line to get the job done. Arthur meanwhile, is much less worried about being in charge and is happy at first to operate in the background replying to Santa’s letters. However, when a crisis at Christmas emerges and a child does not get the present he is supposed to receive, the very different reactions of Santa’s two sons provides us with an insight in to two very different management approaches. One approach endorsed by Steve is to stick to the rules and not risk wider failure for the sake of just one child (a sort of utilitarian approach which most management processes are based upon). Arthur’s approach, meanwhile, is to remember the true spirit of Christmas and to ensure that every child is important in their own right – perhaps a more deontological Kantian approach to present delivery! Ultimately, the film (like Storks) does have lessons in leadership that challenge the sort of macho, utilitarian, top-down approaches that have come to dominate management practice. 

38. Warden Norton (The Shawshank Redemption, 1994) 

 “I believe in two things: discipline and the Bible. Here you’ll receive both. Put your trust in the Lord; your ass belongs to me.”

The Shawshank Redemption is based upon the Stephen King novella Rita Hayworth and the Shawshank Redemption and it follows the prison life of Andy Dufresne – an accountant, wrongly convicted of murdering his wife. The film rights were purchased by director Frank Darabont with a five thousand dollar cheque that was never actually cashed by King – instead according to a Wall Street Journal profile “years after Shawshank came out, the author got the check framed and mailed it back to the director [Darabont] with a note inscribed: ‘In case you ever need bail money. Love, Steve.’” Shawshank is one of those wonderful films that received a lukewarm (and even negative) response from critics when it was first released but which was universally adored by the general public. I can only surmise that critics – often attracted to gritty realism – disliked the uplifting ending of the film and if they had been writing/directing it Andy would have hanged himself in the hotel room. But alas he didn’t and it went on to become the highest ranking film of all time on the Internet Movie Database (IMDB), above The Godfather, above Citizen Kane and all the others. Film critic Mark Kermode has suggested in his book about the film that one of the reasons for the success of the film can be found in the religious symbolism in the film, with Dufresne being portrayed as a Christ-like figure throughout, wrongly convicted, tortured, selfless, sacrificing but ultimately finding his own redemption through struggle, which Kermode argues has a sort of universal appeal particularly amongst western audiences. 

If Dufresne is the Christ figure of the film Warden Norton (played by Bob Gunton) – the sadistic, authoritarian prison boss – could perhaps be seen as the Pontius Pilate figure of the film. From the outset on Dufresne’s arrival at the prison he says in one of his many quotable lines “I believe in two things: discipline and the Bible. Here you’ll receive both. Put your trust in the Lord; your ass belongs to me.” He has extremely strict rules which the prisoners must adhere to and which he gives a free rein to his even more sadistic guards to enforce. He portrays himself as a religious man but in many respects this is merely a cover story so that he appears an upstanding member of the community – in truth, he is cooking the books and making as much money as he can from prison labour. Discovering Andy has talents for accountancy he “hires” him (pro-bono of course) to help write the accounts and ensure that he can keep getting away with embezzling money. In one famous scene Andy grows frustrated at his boss’s behaviour and, forgetting his situation, accuses the warden of being obtuse. The warden subsequently ensures he is severely punished putting him in solitary confinement (and murdering one of his friends). He arrives at Dufresne’s cell to give him the news and tells him he must continue to work for him or he will make his life a living hell. He finishes by saying menacingly: “you understand me, you catching my drift…or am I being obtuse?”.  In one article Gunton revealed that to this day people still come up to him at airports and all manner of places with wry smiles asking him if he is being “obtuse”.

King and Darabont’s portrayal of a rule-driven manager here is a common example of a manager that thinks the rules apply stringently to everyone but himself. The rules are primarily used as a tool of domination and to open up space for the individual to act in ways that others can’t in order to take advantage of the situation. Thankfully, Norton gets his comeuppance eventually with Andy making an escape from the prison but not before ensuring that his bosses books are positively “un-cooked” and sent off to the authorities. Andy even gets his own back on Norton by withdrawing his money on the outside to start a new life and leaves his beleaguered boss with police cars approaching with only one very final way out. 

39. Dave Harken (Horrible Bosses, 2011) 

“Listen to me, you stupid little runt. I OWN YOU. You’re my BITCH! So don’t walk around here thinking you have free will because you DON’T. I can break you anytime I want!”

This is the third and final time Kevin Spacey appears on the list – this time as horrible boss Dave Harken. The film has already been discussed but this particular horrible boss is awful insofar that he uses his position as president of Comnidyne to enforce rules to make his employee’s lives a misery. He punishes one member of staff for being two minutes late to work and makes him turn in to his job on one occasion so that he misses his own grandmother’s funeral. He also frequently uses extremely annoying managerial mottos such as: “You can’t run a marathon without putting some Band-aids on your nipples.” 

40. Ebenezer Scrooge (The Muppets Christmas Carol, 1992) 

“Christmas is a very busy time for us, Mr. Cratchit. People preparing feasts, giving parties, spending the mortgage money on frivolities. One might say that December is the foreclosure season. Harvest time for the money-lenders.”

If you were to go back in time and tell Charles Dickens that a hundred fifty years later one of the definitive interpretations of his novella A Christmas Carol was acted out primarily through puppets, you might forgive him for being both confused and disappointed. After all, he intended the work to be a piece of fierce social criticism which would shine a light on child poverty in Victorian England. And yet, it is now widely believed that Jim Henson’s version of the classic tale told primarily through ‘muppets’ (and Michael Caine as Scrooge) not only managed to tell the story in one of the most entertaining and accessible ways to date, it actually managed to keep closest to the original source material. Dickens’ inspiration for A Christmas Carol came from visiting factories in Manchester and experiencing the severe poverty and terrible working conditions during the 1840s in what was considered a great depression in England. The film (following the book) opens with the miserly Ebenezer Scrooge who suggests that poor people unable to work should go ahead die and thereby “decrease the surplus population.” Scrooge runs his money lending firm with an iron fist and treats his employee Bob Cratchit terribly, paying him low wages leaving him unable to properly fund the medical care of his infant son, “tiny” Tim. Dickens’ inspiration for this character was his own disabled nephew, who unlike Tim did not survive the difficulties of being a young disabled person in the Victorian era. 

One of the targets of Dickens’ book was the inaction and lack of care of business men like Scrooge who were living by one set of rules – every man and woman for themselves – that had become dangerously ingrained in the social fabric of Victorian Britain. A blind devotion to these capitalist and social Darwinist perspectives had been educated in to Scrooge from a very young age: to make it in business you had to be ruthless and people were merely a means to an end, namely creating profit. The portrayal of Scrooge follows the traditional route of him encountering the three ghosts of Christmas (past, present and those yet to come) slowly realising  the misery living by such rules had created for his workers, his family and even himself. Dickens core message within the book is that there is greater happiness for all if we are to adopt a rule of kindness and care for others. After watching and presumably enjoying this wonderful version of his novella it would perhaps be more disappointing to Charles Dickens to learn that many of the problems around child poverty and exploitation still exist today and that many of its core messages are still as relevant today as they’ve ever been.

Identity Five: The Greedy Boss

In recent years greed has become synonymous with the boss, particularly following the financial crisis in which many CEOs and directors contributed towards the severity of the crash through sheer recklessness in the aim of extending their wealth. Many bosses continued to rake in tens of millions of dollars in bonuses all while the taxpayer spent billions bailing out the companies which they had run in to the ground. The figures involved here are eye-watering and while not a single CEO went to jail after the 2008 crash this brazen behaviour cemented the idea of the greedy, corrupt manager in the modern public mind. And yet, this is by no means a new phenomenon. One could even argue that the insolvency of the Medici Bank in 1494 – perhaps one earliest corporate scandals/collapses on record – was caused by the complete mis-management of the bank encouraged by the greed and extravagant lifestyles of the Medici family. Similarly, the collapse of the British South Sea Company in 1720 and the subsequent South Sea bubble stock market crash was precipitated by fraudulent activity by leaders within government and speculators seeking to greedily capitalise by misleading individuals about actual levels of trade. In short, greed within the managerial class extends back to the very roots of capitalism and being a manager has often become synonymous with being hungry for money and using power to accumulate wealth. 

Many of the previously mentioned bosses would also fit under this heading, but these managers stood out to me for their need for money above all else:  

41. Johnny Friendly (On the Waterfront, 1954) 

“Where you guys going? Wait a minute! I’ll remember this! I’ll remember every one of you! I’ll be back! Don’t forget that! I’ll be back!”

On the Waterfront, directed by Elia Kazan is one of the most controversial Hollywood films ever made. It stars Marlon Brando as Terry Malloy, an up and coming boxer who is convinced by a local mob boss, Johnny Friendly (played by Lee J. Cobb), to throw a fight so that he can make his fortune with the local bookmakers. A longshoreman is subsequently murdered on the docks where they all work and Malloy (knowing Friendly is behind it) is gradually convinced that it is “the right thing to do” to speak out against the corrupt gangster, who runs the docks with an iron-fist for his own financial benefit. The first reason for the film’s controversy is that it is widely known to be an apologia for Kazan’s own naming of names in the House of Unamerican Activities Committee in the 1952. Led by Senator Joseph McCarthy these trials called people to court to testify and reveal communists supposedly hidden in plain sight of every day American life. At the height of the red scare Kazan was called to inform on a theatre group he had been a member of in the 1930s and after much deliberation decided that it was the right thing to do, not only to save his own career – which would have been destroyed if he had refused to do so – but also (according to him) because he genuinely believed them to be communists. The film, then, had been received immediately in 1954 as a justification of Kazan’s actions, to inform on people like Johnny Friendly, whose corruption were deemed as degradational to the American way of life. 

The second reason for the controversy surrounding the film is for a much better reason: the method acting of Marlon Brando rarely seen anywhere in Hollywood before this film. I can recall now seeing this film for the first time (in the mid-nineties as a teenager) and watching Malloy (Brando) walk along with his co-star Evie Marie Saint. In the scene Saint accidentally drops a glove and rather than hand it back to his co-star he keeps it, plays with it and slides it on, continuing the scene. He eventually returns it towards the end. Brando’s more natural approach to acting jars fantastically well with his other male co-stars in the film, especially Cobb (Friendly), and makes you sympathise with his decision to name names. Perhaps his decision was a much more justifiable one than Kazan’s – informing on a greedy, murdering mobster is somewhat different to the kind of informing Kazan did. And yet according to one article, in his autobiography, Kazan apparently noted: “On the Waterfront was my own story; every day I worked on that film, I was telling the world where I stood and my critics to go fuck themselves.” Perhaps, many in Hollywood would argue that rather than Kazan being the hero of the story (he imagined himself in the Malloy role), in selling out his friends in order to continue his successful career, he may in fact reflect the greedy and corrupt nature of the film’s central villain, Friendly. One screenwriter Abe Polonsky may have agreed with this in particular. He is rumoured to have said: “If I was on a desert island with [kazan], I’d be afraid to fall asleep because he’d probably eat me for breakfast.” 

42. Will Emerson (Margin Call, 2011)  

“The only reason that they all get to continue living like kings is cause we got our fingers on the scales in their favour. I take my hand off and then the whole world gets really fucking fair really fucking quickly and nobody actually wants that. They say they do but they don’t. They want what we have to give them but they also wanna, you know, play innocent and pretend they have no idea where it came from.”

J.C Chandor’s 2012 Margin Call is set at the heart of the 2008 financial crisis – specifically within the 24 hour period where the sheer size of the problem facing the sector and indeed the world was uncovered. The organization explored resembles Lehman Brothers in every way (but is not named). The film begins with a recently fired boss handing off a firestick with information on to entry level analyst, Peter Sullivan (Zachary Quinto). From here, Sullivan learns from the data on the stick that the situation is grave – a full on financial crisis is more or less unavoidable. The story told hereafter is a cautionary tale therefore, about the greed and excesses of Wall Street and the financial sector at large, who had become exposed way beyond its means. Will Emerson (played by Paul Bettany) is Head of Trading at the firm and plays a fascinating role within the film of almost being an apologist for the actions of the bank and the bankers – pushing the blame instead to the greed of wider society. In the scene (in which the quote above is spoken), he tells a junior colleague Seth Bregman (played by Penn Badgley) that he is certain to be fired, but everything will be okay. When Bregman says he feels sorry for the wider public who will suffer the financial fall-out of the coming “crash” he explains that normal people (presumably in the West) need the big banks to do well or their cushy lifestyles will be under threat. He says:

That’s more hypocrisy than I’m willing to swallow so fuck them…fuck normal people. You know the funny thing is if all of this goes tits up they are going to crucify us for being too reckless, but if we are wrong and everything goes back on track, well the same people are going to laugh until the piss their pants, because we are going to look like the biggest pussies that god ever let through the door.

In what appears to be the internal justification of a head trader Emerson tells Bregman, ‘you have to believe you are necessary’. That their greed was necessary, and someday (when the financial crash passes) it will be necessary again. Considering very little has changed since 2008 in the financial sector and it remains as dangerously exposed as it was in 2008, it seems that the internal logic of Emerson’s claims (and the financial sector at large) remain unchanged. It is the ongoing greedy quid pro quo for the 1 percent – of which on a global scale I (and probably most others reading this) are part of. It is a sobering film, and the greed of Emerson and the internal logic he reveals is something that governments and all of us almost certainly need to reflect upon. 

43. Sir Richard McReadie (Greed, 2020)  

“I pay what I have to and no more ’cause I’m not stupid. If you want to chase people avoiding tax, why don’t you go after the big boys? I mean, look at Apple. Look at Amazon, Starbucks. Talk to Bono. He’s avoided hundreds of millions of tax by claiming that U2 are based in Holland. Doesn’t stop him going around the world in your nan’s sunglasses proclaiming about ending poverty or whatever.”

Ironically, greed and the accumulation of wealth within the identity of the boss can also be coupled with their desire to spend vast amounts of money. It is common to see depictions of the greedy manager splurging money in order to gain reputation, friends and whatever else it brings. For instance, in 2012 Vogue reported on billionaire and Topshop owner Sir Philip Green’s latest party:

Sir Philip Green celebrated his 60th birthday this weekend with what was unarguably one of fashion’s most extravagant parties – a four-day extravaganza, attended by Leonardo Dicaprio, Kate Moss, Naomi Campbell, Kate Hudson, Ronnie Wood, Gwyneth Paltrow and Simon Cowell. As previously reported, guests were told to arrive at Luton airport with their passports and a suitcase of clothes suitable for “warm weather” and were flown to a then unknown destination – which turned out to be an idyllic beach resort in Mexico. Attendees were also asked to provide their personal measurements, thought to be for tailor-made fancy dress costumes. According to the Daily Mail and the Telegraph, entertainment included performances from Stevie Wonder, Bruno Mars, Robbie Williams, Cee Lo Green, George Michael, Enrique Iglesias and Rihanna as well as a spectacular fireworks display – all of which cost a reported £3 million. Guests, including Kate Hudson, Leonardo DiCaprio and Naomi Campbell, were spotted playing games on the beach this weekend.

Michael Winterbottom’s satirical comedy film Greed delves in to this world directly showing us a character McReadie (played by Steve Coogan) who is directly inspired by Green. It intersperses clips of McReadie eagerly planning his latest party with clips of workers in sweat shops making the clothes on which his immense wealth is built. Topshop, the fashion outlet that Green owns, has reportedly used child labour in the past and paid its mostly female Sri Lankan employees a meagre 40p an hour

Coogan has suggested in an interview that he is not so bothered about ‘Philip Green as an individual. [He is] interested in the system that allows people like him to thrive…Even if Philip Green has some weird epiphany or some conversion — which is not going to happen — even if he did, it wouldn’t make much difference to the system.” The film explores the dark greed at the heart of many of the most well-known fashion brands on the high street that continue to sell clothes in massive numbers to a general public who know of their indiscretions in the third world but (like me) seek out high quality garments at low prices. Winterbottom, who also wrote the film, asked with some incredulity: ‘How is it that a guy who runs a company is worth $60 billion and the women making the clothes for that company are getting paid $3.50 a day?’ In making the film, he said ‘It felt very simple to make the link between those kinds of facts and figures with specific examples.’ The film also highlights the tax loopholes that managers of companies like Topshop but also Google and Amazon use to accumulate wealth in such massive amounts with direct consequences on the public finances of the countries in which they reside. Rather frustratingly, it doesn’t seem like the Philip Greens of this world care in the slightest about their depictions in films of this kind. A friend of Green told one newspaper that “He says he’s not interested in it and…I don’t think it’ll be on at his local cinema in Monaco, so he won’t have to try too hard to avoid it.” 

44. President Business (The Lego Movie, 2014) 

‘Let’s take extra care to follow the instructions or you’ll be put to sleep, and don’t forget Taco Tuesday’s coming next week’

The supremely innovative The Lego Movie was the first blockbuster movie to be made (almost) entirely from Lego pieces with stop- go animation techniques. Whilst the film is more-or-less a 100 minute advert for Lego, it is also hilarious and, like many “children’s movies” surprisingly inciteful. President Business, the antagonist and villain of the animated film, is ‘president of the Octan Corporation and the world’ . The hero of the film Emmet, is pitted against him in a desperate quest to stop Business from using the “Kragl” – a super weapon, which turns out to be crazy glue that could potentially be used to glue the Lego bricks together freezing things exactly as they are. A permanent state of business supremacy. One of the most fascinating things about the film is that in a surprise twist we learn that President business and the whole constructed Lego world is that of a “real” child who enjoys constructing and reconstructing this world in his basement. He is ultimately scared that his dad (“the man upstairs”, also the voice of president business) is going to use the Kragl (Crazy glue) to freeze bricks together so he can preserve his own unique creation. Without getting too deep (about The Lego Movie!), one could read in to the film that it has a theme around inter-generational justice in which children want a future that they can imagine to be made and re-made (as they do with Lego) and that gluing the pieces together (and preserving business as usual forever) it is robbing the boy of his imagination, fun and (at least in the boy’s mind) his future dreams. The old man upstairs is president business, a curmudgeonly boss-like figure wanting the world to stay as is with him greedily keeping things in a permanent status quo that suits his own needs. Or maybe it’s just a film about Lego! 

45. Mr Krabs (SpongeBob SquarePants, 1999)  

[Singing about money] “counting me money. Money sweeter than honey. Money money this, money money that. Profit will make me wallet fat”

SpongeBob SquarePants is a cult animation TV series popular with children and (largely stoned) adults. It follows the adventures of aforementioned SpongeBob and his friends who inhabit the underwater city of Bikini Bottom. Created by marine biologist and animator Stephen Hillenberg, Mr Krabs is a restaurant owner and boss of an establishment called The Chum Bucket. Mr Krabs is obsessed with money. In one scene (here are a few of his best bits) he is literally woken back up after feinting by wafting a twenty dollar note under his nose. In her book A Research Agenda for Management and Organization Studies Barbara Czarniawska describes Mr Krabs as “a ruthless capitalist who exploits his customers and his workers alike” and considers the way as a manager he takes advantage of others in order to accumulate wealth.  In a 2006 Huffington Post Article about which way each SpongeBob character would vote in an American Election, voice artist for SpongeBob, Tom Kenny, suggests it would undoubtedly be Republican. He is, ‘like Halliburton,” laughs Tom. “He’s unchecked, unthinking, unregulated capitalism. Everything is about the bottom line, not about what’s socially responsible. I mean if you have to turn a couple school sites radioactive in the pursuit of profit or destroy a Great Lake or two… it’s just business; nothing personal.’ The continued negative representation of bosses in children’s animation as greedy is a fascinating phenomenon, one that is perhaps a reflection of the reality we live in but maybe also a productive phenomenon of how children might see future managers, what they expect them to be, or perhaps (more worryingly!), how they see themselves in these roles someday – accumulating wealth at the expense of anyone that stands in their way.

46. Mr Potter (It’s a Wonderful Life, 1946) 

“Look at you. You used to be so cocky. You were going to go out and conquer the world! You once called me a warped, frustrated, old man. What are you but a warped, frustrated young man? A miserable little clerk, crawling in here on your hands and knees and begging for help”

The consistent association of greed and avarice with management figures in Hollywood has not gone un-noticed, especially by government authorities. In a 1947 FBI memo regarding an evaluation of several Hollywood films it was stated: “With regard to the picture ‘It’s A Wonderful Life’, [the informant] stated in substance that the film represented a rather obvious attempt to discredit bankers by casting Lionel Barrymore as a ‘scrooge-type’ so that he would be the most hated man in the picture. This, according to these sources, is a common trick used by Communists….In summary, [the informant] stated that it was not necessary to make the banker such a mean character and ‘I would never have done it that way.’” Potter is undoubtedly cast as the villain of the film opposite the everyman hero George Bailey (played by James Stewart). Potter wants to repossess Bailey’s business and Bailey seeing no other way out, considers suicide. Thankfully, his guardian angel, Clarence, is on standby to show just how important Bailey’s life has been by showing him how bad it would have been if he had never existed. The core message of the film is that no matter how bad things get in life, it is important to “not let the bastards grind you down” – in this case, the bastards being heartless bank managers. 

Interestingly, the FBI memo goes on to make another pertinent observation: “The purpose of the Communists in Hollywood is not the production of political movies openly advocating Communism. Their purpose is to corrupt non-political movies — by introducing small, casual bits of propaganda into innocent stories and to make people absorb the basic principles of Collectivism by indirection and implication. Few people would take Communism straight, but a constant stream of hints, lines, touches and suggestions battering the public from the screen will act like drops of water that split a rock if continued long enough. The rock that they are trying to split is Americanism.” This is especially interesting as our very own research techniques to explore the representation of bosses and work in movies have tended to look for representations in a similar way. We have preferred to seek out the  less obvious depictions and pick up on the smaller scenes which might uncover the unconscious biases or reflections of the film makers approaches. It turns out that my colleague and I have been implementing FBI research techniques all along – something for the next methodology section! 

47. Avery Tolar (The Firm, 1993)  

“Being a tax lawyer’s got nothing to do with the law. It’s a game. It’s a game. We teach the rich how to play it so they can stay rich. The IRS keeps changing the rules so we can keep getting rich teach them. It’s a game…”

Avery Tolar (played by Gene Hackman) is the head of Bendini, Lambert and Locke law firm which specialises in tax accounting. Tolar hires young hot-shot lawyer Mitch McDeere (played by Tom Cruise) who is recruited to the firm through various lavish incentives including a new house and car and the possibility of rising to be the youngest partner in the firm’s history. However, once he is inside the firm Mitch learns from his boss that most of the firm’s business is through helping wealthy clients (many of them mafia related) to hide their money in the Cayman Islands. The firm is essentially a massive money laundering and tax fraud operation. Mitch then begins to notice that a worryingly high number of his fellow lawyers are dying in “accidents” and that, as he finally realises, nobody ever leaves the firm alive. Instead, the direct aim of the firm is to hire young, money-hungry lawyers (often from poorer backgrounds) lavish them with money and gifts and then use them to launder money unable to speak out without risking prosecution themselves. Even Tolar is eventually killed by the firm, which ultimately shows that whilst he appeared to be the man in charge, he too was wrapped up in the same game as all the other lawyers, who had been recruited through the seduction of money and lifestyle, trained how to launder and commit fraud and then discarded once they had become too big of a risk. 

When the film was released in 1993 the LA Times ran an article asking real-life lawyers how accurate of a portrayal the film was of their own working lives. As one respondent from a tax attorney office stated: “I don’t know anybody that leads the lifestyle that they led…that’s Hollywood, and John Grisham.” Another went on to add  “If they made (“The Firm”) realistic, it would be people sitting around in a library–and nobody would want to watch it.” This is a common issue within films and TV show, that they portray professions as significantly more exciting than they are in reality. Shows like Ally McBeal similarly glamorised the legal profession in the 90s and shows like CSI and Silent Witness have led to a surge in degrees in forensic sciences, despite being extremely different to the realities and requirements of the job. One can imagine that there are a lot of disappointed and incredibly bored forensic scientists and lawyers out there today thinking this really is not what I imagined (or saw!) it to be. Interestingly, John Grisham’s novel the firm ended with Mitch and his wife living a lavish new life in the Cayman Islands with the 10 million dollars they had more or less taken for themselves. The film shies away from this conclusion, instead having Mitch and his wife return to Boston free from the firm and the threat of prosecution. Perhaps there are limits to the amount of “reward” we want to see the hero of a film receive for essentially following a route inspired by greed.   

48. Claire Dearing (Jurassic World, 2015) 

Claire: “We’ve been pre-booking tickets for months. The park needs a new attraction every few years in order to reinvigorate the public’s interest. Kind of like the space program. Corporate felt genetic modification would up the wow factor.” 

Owen: “”They’re dinosaurs. Wow enough. 

Claire: “Not according to our focus groups. The Indominus Rex makes us relevant again”

Often the evolution of a managerial character is one of the most interesting aspects to observe and understand. It reveals what are considered to be culturally disliked traits in managerial attitudes and then later what we might like them to look like in an ideal world. Ebenezer Scrooge is a good example of this kind of evolution and we have already covered this particular journey above, reflecting how managers can be saved and rehabilitated if the shock they experience is enough to jolt them out of their ways. Claire Dearing (played by Bryce Dallas Howard) is another such character who evolves in front of our eyes across a trilogy of films beginning with Jurassic World. In first of these films, we encounter Dearing as the park operations manager of a dinosaur theme park, with genetically re-created “real” dinosaurs – a bit like a giant zoo but with T-Rexs and velociraptors. She is a workaholic, neglecting her family and wider life and considers the dinosaurs to be assets to be used to create as much profit for the company as possible. However, when a dinosaur escapes and rampages through the park, she begins to realise that these are living, thinking beings and that she has made a costly mistake. The film essentially places a corporate manager way outside of her comfort zone dropping her in with the terrifying reality of the dinosaurs. In one interview Howard reveals how she was the central reason Dearing spends half the film running through the jungle in high heels. She explains, “I was reading [the script] and I was like ‘No…no it’s an office, Claire would wear heels.’ And then it was like another scene where I’m like ‘hmm, well Claire’s kind of like…she’s going to wear heels in this scene also.’” This led to a movie where we have a traditionally dressed female manager being chased by dinosaurs through the jungle – a rather bizarre image to say the least! 

By the end of the first movie, the corporate veneer of Dearing has been shattered by her experiences and instead of greedily exploiting the dinosaurs she now wishes to devote her life to protecting the welfare of them around the globe. In a later interview around the release of Jurassic World 2 Howard explains how she tried to “learn more about people who had moved out of management and in to a more meaningful job. I talked to some folks who have become activists as their career, as their life’s mission. And usually there is that defining moment, where they’re like, ‘Yeah, I had a corporate job, and I didn’t stop and smell the roses, and all this kind of stuff, and then this big event happened, and I realized, basically, who I was and what I believed in.’ There is a clear attempt here to shape a fictional account of the evolution of a corporate manager on the experiences of real-world managers who might have done similar – although it’s hard to imagine her finding managers who had quite gone through what Dearing had inside Jurassic Park! 

49. John Tuld (Margin Call, 2011) 

“So you think we might have put a few people out of business today. That it’s all for naught. You’ve been doing that every day for almost forty years Sam. And if this is all for naught then so is everything out there. It’s just money’ it’s made up. Pieces of paper with pictures on it so we don’t have to kill each other just to get something to eat. It’s not wrong. And it’s certainly no different today that it’s ever been. 1637, 1797, 1819, 37, 57, 84, 1901, 07,29, 1937, 1974, 1987 – Jesus, didn’t that fuck me up good – 92, 97, 2000 and whatever we want to call this. It’s all just the same thing over and over; we can’t help ourselves. And you can’t control it, or stop it, or even slow it. Or even ever-so-slightly alter it. We just react. And we make a lot of money if we get it right. And we get left by the side of the road if we get it wrong. And there have always been and there always will be the same percentage of winners and losers. Happy foxes and sad sacks. Fat cats and starving dogs in this world. Yeah, there may be more of us today than there’s ever been. But the percentages – they stay the same”. 

The somewhat poorly disguised inspiration for John Tuld in the aforementioned Margin Call is none other than Dick Tuld, former CEO of Lehman Brothers. Also, known as the “Gorilla of Wall Street” he had built up a reputation as a no-nonsense CEO with a ferocious disposition but was subsequently held responsible for Lehman Brother’s role in the sub-prime mortgage crisis and resulting world financial crisis of 2008. Whilst testifying to the American house oversight and government reform committee he absolved himself of all blame instead claiming ‘a perfect storm of other factors’ and that ‘nobody including me, anticipated how problems in the mortgage markets would spread to our credit markets…and now threaten our whole financial system.’ This is consistent with the characterisation of boss John Tuld (played by Jeremy Irons) in Margin Call, shifting responsibility from himself and others at the top of the organization to the wider structural conditions he found himself in. It points towards a sort of purposefully adopted naivety (almost certainly an act) which allows a manager to claim no knowledge of individual wrongdoing. As a Forbes article reviewing the film suggests, the running joke within Margin Call is that “the higher up an executive is on the corporate totem pole, the less likely he is to understand how the firm and its traders cook up the toxic brew of mortgage-backed securities. Their ignorance seems almost a point of pride for the executives.” Simply put, in the world of high stakes banking ignorance really is bliss. According to one profile of Tuld (the real one that is), whilst being considered one of the worst CEOs in baking history he still walked away with half a billion dollars in bonuses and compensation and today is back working on Wall Street of the CEO of a smaller version of Lehman Brothers. 

50. Jared Vennett (The Big Short, 2015) 

“When you come for the payday, I’m gonna rip your eyes out. I’m gonna make a fortune. The good news is Vinnie, you’re not going to care cause you’re gonna make so much money. That’s what I get out of it. Wanna know what you get out of it? You get the ice cream, the hot fudge, the banana and the nuts. Right now I get the sprinkles and yea – if this goes through, I get the cherry. But you get the sundae Vinny. You get the sundae”

The Big Short is a 2015 film which covers similar ground to Margin Call, attempting to understand how such a massive financial crisis could take so many people by surprise. The film is based on Michael Lewis’s book of the same name (with the subtitle “Inside the Doomsday Machine”). Jared Vennett (played by Ryan Gosling) is hedge fund manager at Deutsche Bank. We get an insider account of the build-up of the subprime mortgage crisis as people realise that the US housing market is a bubble supported by unsustainable and soon-to-fail loans. Once aware of this fact, we see how a small group of people were able to make huge amounts of money by betting against the housing market – shorting it – so that when the bubble burst they were in place to make a fortune.  A detailed blog about what Vennett/Lipmann actually did is available here – it is far too complicated (and let’s be honest slightly boring!) to type out in full here. The interesting thing to me, in terms of the cultural representation of the greedy manager is that Lipmann has since gone on record at the time as saying: “I don’t have any particular allegiance to Deutsche Bank, I just work here.” He has since moved on, as many other managers of the time have, to make their fortunes through another scheme – whilst the people who truly suffered as a result of the financial crisis (that lost their homes in the bubble) had no such luxury. Instead, for financiers like Lipmann the hunt is on now for the next “big short” and he has already had his say on this. In one clip he can be seen advising the money hungry folks who want to follow in his footsteps, suggesting it might be found in shorting consumer debt. 

51. Duke of Weselton (Frozen, 2013)  

“Open those gates so I may unlock your secrets and exploit your riches! Did I say that out loud?”

The fact that this is the fourth Disney manager to be explored in this list reflects just how pre-occupied the writers of Disney films are with organizational leaders. I have long suspected this is because the history of Disney as a corporation and as a cultural phenomenon is wrapped up with a strong and forceful leader in Walt Disney. The Duke of Weselton, whilst in a somewhat smaller role than the likes of Cruella De Vil, follows in the footsteps of other horrible Disney bosses. When the two princesses parents die in a tragic accident it is Weselton who hovers close like a vulture waiting to exploit their riches. Weselton is also portrayed as a much more ridiculous character than previous Disney bosses, as his greed is mocked repeatedly and shown as a reflection of his cowardice and all round lack of values. 

52. Thomas Sandefur (The Insider, 1999) 

“I joined Brown & Williamson, came up through sales. I was the best salesman they ever had, and do you know why? I never made a promise I couldn’t keep – and if I did, I would accept the consequences”

Thomas Sandefur’s New York Times obituary recounts how in 1994 he sat before a congressional committee with six other heads of tobacco firms and declared: “I believe nicotine is not addictive…I am entitled to express that view, even though it may differ from the opinions of others.” The Insider is a film which explores the unrepentant greed of tobacco company bosses who continued to sell cigarettes without warning to a customer base that had little to no idea of the carcinogenic effects of their products. Insider Jeffery Wigand (played by Russell Crowe) is a research chemist within the organization and is invited to turn whistle-blower on a national news show 60 minutes. Sandefur (played by Michael Gambon) is Wigand’s boss and the head of Brown and Williamson Tobacco. On suspecting something is afoot Sandefur calls Wigand to his office attempting to dissuade him from betraying the company in what amounts to one of the best onscreen representations of corporate bullying. Wigand relies on the corporation for his wage and most importantly medical insurance for himself and his sick child, and he also fears being sued by a powerful multinational corporation. He finds himself in a complex ethical dilemma where he is stuck between weighing the well-being of the general public against the well-being of his own family. 

The movie suggests that the bosses at Brown and Williamson were so worried about the revelations that they actively issued death threats towards Wigand, with Crowe’s character in the film finding a bullet in his mailbox. The television network was also repeatedly threatened with legal action at one point leading them to shelve the already recorded interview. On the film’s release, this depiction of Brown and Williamson (and Sandefur) who were depicted without any changes of name created serious problems for the film’s distributors, Disney studios. Brown and Williamson were keen to sue for libel it effected their sales in any way, and were insistent that they had not gone as far as the film had suggested. One company spokesman Steve Kottak suggested: “We’re seeing what effect this movie may have on our company. It clearly suggests that we threatened Jeffrey Wigand, our former employer. It suggests we had him followed and put a bullet in his mailbox. It didn’t happen. We never threatened Jeffrey Wigand or his family in any way.” It was even reported that the tobacco company even went as far as polling audience members as they left cinemas to see whether their views of the organization had changed or not. However, if Brown and Williamson/Sandefur decided to sue it would only support the main contention of the film – that the tobacco industry were bullies who tried to silence people – and turn it in to a bigger hit that would be watched by even more people. The legal action was quietly dropped but not without a making a clear impact on Disney Studio’s CEO, Michael Eisner. One source reported that he regretted green-lighting the film and that his attitude to the whole fiasco was ‘Jesus, it’s been a pain in the ass for me, I’m sorry we ever made the fucking thing’ and ironically it ‘was his frustration at the lack of money it appears to be making.’ So it seems whether it’s the movie business or the tobacco industry, many bosses weigh success purely in terms of money.

Identity Six: The Renegade Boss 

Bosses are not always rule-following conformists. They sometimes forge an identity around breaking the rules in order to innovate and do away with stale and outdated practices. Buckingham and Coffman’s 1999 book “First Break all the Rules” encourages bosses to embrace deviation, and doing things differently. They argue, based on empirical evidence, that the most successful bosses in the world today do not merely toe the line, but challenge conventional wisdom and do things that might surprise or shock. What they consider “success” in the workplace is less clear however. There are also limits to the benefits of renegade behaviour, and knowing where the limits are without self-destructing or causing organizational damage. The obvious problem with being a renegade bon is that if things go wrong, you become the target for blame, especially by people who have forged identities around conformity and more conservative practices in the workplace. There is some evidence that preference for renegade managerial strategies are influenced by national culture, with individualistic (anglo-sphere) countries preferring renegade management and collectivist countries preferring a more rational, logical and predictable approach to managing. There are examples which undermine such a claim however, when we consider renegade management or leadership in radical democratic organizations. For instance, Brazilian businessman Ricardo Semler introduced a range of democratic measures in his company, encouraging more collectivist behaviours through a managerial identity that actively sought to break with conformity. His own account of these changes within Semco are explored within his book Maverick, in which he actively cultivates this image of himself as a renegade boss. 

So, whilst bosses are often portrayed as being rather dull (of being “men in grey suits”) in a more fantastical sense they are also imagined as individuals who can break the mould and do something completely different. In doing so, they tend to walk the line between legality and illegality but – they would argue at least – they are doing so for what they consider to be the greater good. Here are ten examples of renegade bosses from TV and film that not only ignore the rule book, they burned it, buried it and never looked back: 

53. John Milton (The Devil’s Advocate, 1997) 

“Let me give you a little inside information about God. God likes to watch. He’s a prankster. Think about it. He gives man instincts. He gives you this extraordinary gift, and then what does He do, I swear for His own amusement, His own private, cosmic gag reel, He sets the rules in opposition. It’s the goof of all time. Look, but don’t touch. Touch, but don’t taste. Taste, don’t swallow. Ahaha. And while you’re jumpin’ from one foot to the next, what is He doing? He’s laughin’ His sick f-ckin’ ass off! He’s a tight-ass! He’s a SADIST! He’s an absentee landlord! Worship that? NEVER!”

Who better to be our first renegade boss than Satan himself? The first rebel in recorded history re-imagined as a senior partner of a law firm in downtown New York. The film begins with Kevin Lomax (played by Keanu Reeves), a hot-shot unbeaten lawyer who is tempted through various means to join John Milton (subtle as a brick…) at his law firm Milton, Chadwick and Waters. At first they tempt him to come and select a jury for them that can secure the freedom of one of their less than reputable clients and subsequently they offer him a huge salary and apartment to move him and his partner to the city. Lomax then increasingly finds himself in difficult cases defending what seems like the indefensible and using his substantial legal skills to get murderers and rapists off the hook. Ultimately we learn that Lomax gains he owes his legal skills to his illegitimate father he had never met – John Milton (Satan). Much has been written about whether Devil’s advocate unfairly gives legal firms and in particular defence lawyers a bad rap, and that it is merely party of a wider trope of lawyers  and law firms as the enemy. Here, rather than completely demonising the law firm (as happened in The Firm), The Devil’s Advocate is different insofar that it literally does make you have sympathy for the Devil (particularly in this speech, one of my favourites of all time).  

It’s a film about rebellion from the system, and Lomax represents the ultimate rejection when he finally walks away from his boss (and as we learn father) Milton, ruining all of his plans of world domination. The final scene of the film, which rewinds to the very beginning of the film with Milton taking another shot at convincing his son to join him talks to the inescapability of these ethical dilemmas that haunt us all, in wanting to break free but failing to do. Ultimately, we have two routes to being a renegade here: we can rebel against the current system of management or we can rebel against those seeking to replace it when we know they too are wrong. In some ways, the second route is the most difficult path to take but many of us take it time and time again like Lomax in what reflects a Nietzschean eternal recurrence. 

54. Gus Fring (Breaking Bad, 2008) 

“I Investigate Everyone With Whom I Do Business. What Careful Man Wouldn’t?”

Gus Fring (played by Giancarlo Esposito) is the owner and boss of a chain of fast-food chicken restaurants. He is also one of the biggest distributors of meth-amphetamine in New Mexico. In fact, these jobs go hand-in-hand, with his role as an upstanding member of the business community enabling Fring to hide in plain sight and distribute his ‘product’ between his various chicken outlets across Albuquerque undetected. Breaking Bad is in essence a show all about seemingly ordinary people who have decided to act outside the boundaries of their expected (legal!) behaviours in order to make money and seek power. So, for instance, the shows lead character Walter White is a chemistry teacher who on learning he has cancer decides that the only way to pay his bills is to make high grade meph-amphetamine with his former high school student, Jesse. Before long they have a considerable amount of meth but little way of distributing it (at least in the quantities required). Walt and Jesse are tipped off about Gus by their underhand lawyer who suggests they pay him a visit at his local chicken store where he seems for all intents and purposes a normal chicken takeaway manager, delivering drinks to tables with a smile. He is, at first, completely unwilling to even acknowledge what Walt and Jesse are talking about – as he is extremely careful about who he does business with – but eventually they convince him to distribute their product leading to a number of amusing and thrilling adventures for all concerned. 

Interestingly, Giancarlo Esposito has talked about his inspiration for playing Fring, suggesting that meth crisis in America was reason enough to take on this character. In one interview he tells us that he read an article about two Mormon missionaries who went off on a mission call and entirely disappeared. A couple of years later they were found living as meth addicts, reflecting a true life “breaking bad” that shows the real depth of the problem and the horror of that specific drug. He also suggests that what attracted him to the character was that he was not a stereotypical villain. Like most renegade managers, despite their immorality and terrible actions we often can’t help but be attracted to their free spirited nature and refusal to play by the rules (perhaps reflecting our own unfulfilled desires to do the same!). Few things are as attractive to workers as managers who refuse to play by the rules – we perhaps imagine having similar bosses and the excitement that it might bring to us rather than having our rule-obsessed, miserly managers that we currently possess. The reality might be somewhat different with having to cope with a manager with whom you had no idea what they would do next (on one occasion Fring calmly undresses out of his business suit in to overalls in complete silence, slits the throat of one of his employees and then calmly in silence gets back changed in to his suit and leaves!). 

Esposito suggests that what also attracted him to the part was that Fring was a man who ‘handled his business like a business”. Those who got in the way of that business paid the ultimate price but those who did well were rewarded. However, in the end those that live by the sword, die by the sword and Fring possibly has the best on-screen death in modern TV history, reportedly requiring 4 and a half hours of make-up to achieve. It’s a scene that is certainly not for the faint hearted and a fitting end for a wonderfully multi-dimensional renegade boss. 

55. Mark Zuckerberg (The Social Network, 2010) 

“I think if your clients want to sit on my shoulders and call themselves tall, they have the right to give it a try – but there’s no requirement that I enjoy sitting here listening to people lie. You have part of my attention – you have the minimum amount.”

It has been noted that Mark Zuckerberg achieved through Facebook in a few short years what the CIA had been trying to achieve for eighty. The immediate and ongoing insight in to the thoughts, likes, dislikes, private affairs of hundreds of millions of people – in an age where information is power Zuckerberg undoubtedly became one of the most powerful men on Earth, becoming a billionaire by the time he was 27. The Social Network revolves around the central question of who came up with the idea and brought it in to existence. There is much debate about the input of previous investors (such as The Winklevoss twins who spent decades suing Zuckerberg over him ‘stealing’ their idea – they eventually settled for $65 million dollars) and the extent to which their involvement shaped the emergence of what become Facebook. When asked about this in an interview Jesse Eisenberg (who played Zuckerberg in the film) suggested ‘my impression from thinking about it as an actor playing the role is that my character is an artist who painted the Mona Lisa, and the [Winklevoss] twins suggested that he paint a woman. No one would ever attribute the Mona Lisa to anybody but Da Vinci, and that’s how I see Mark’s creation. At least in terms of how my character is concerned. I think he strung them along, but no one else could have run it.’ Zuckerberg may have bent the rules but he did so because he was the genius behind the idea and knew how to manage it appropriately and turn it in to something huge – very few other people (if any at the time) could have done that. 

The film, however, did portray Zuckerberg as having mild Asperger’s and being incredibly rude and unthoughtful to most people around him. Zuckerberg himself has expressed hurt at the way the film portrayed him, suggesting that they had ‘just made a bunch of stuff up about [him]’. Jesse Eisenberg (who played Zuckerberg in the film) suggested  ‘he’s not sadistic, malicious, greedy or even overly ambitious. He’s just wired a different way. I feel great sympathy for him’. Some reports have suggested that he is far from the aloof managerial character portrayed in The Social Network arguing that rather than being a tyrant in the workplace he has moved away from hierarchical organizing treating entry level employees as equals, breaking down barriers between executives and regular employees. Whatever people think of Zuckerberg he has broken boundaries and did what no other executive had done before him in terms of penetrating the lives of his customers on such a deep level. Now, he finds himself under attacks over the kinds of messages he allows Facebook users to post and see, with many suggesting by failing to block inflammatory language (by Trump in particular) he is fuelling hate and discrimination. In true Zuckerberg style however, he refuses to play by the rules expected of him and instead continues to play the game of growing Facebook by trying to avoid being drawn in to political debates about right and wrong. Interestingly, the film and character study of Zuckerberg has earned high-praise though and has stood the test of time. In a recent interview Quentin Tarantino suggested it was ‘hands down the best film of the 2010s’. It’s perhaps unsurprising that Tarantino is attracted to a CEO who, like many of his own best characters, refuses to play by the rules of the game and instead makes up his own. 

56. Willy Wonka (Willy Wonka and the Chocolate Factory, 1971) 

“I can’t go on forever, and I don’t really want to try. So who can I trust to run the factory when I leave and take care of the Oompa Loompas for me? Not a grown up. A grown up would want to do everything his own way, not mine. So that’s why I decided a long time ago that I had to find a child. A very honest, loving child, to whom I could tell all my most precious candy making secrets.”

Willy Wonka originally appeared in Roald Dahl’s 1964 book Charlie and the Chocolate Factory, as an eccentric boss and chocolatier. The story was inspired by Dahl’s own childhood in which chocolate companies were wildly protective over their recipes and would send out sample chocolates to young children to test and provide feedback upon. In the book and subsequent film, Wonka (who had closed the factory entirely to outsiders) creates a competition to invite five lucky winners to come inside the factory and see how his chocolate bars are made. All they had to do was find one of the five chocolate bars with a golden ticket. Charlie, an extremely poor child, is one of the winners and so with his Grandpa Joe (who makes a miraculous recovery from his previously bed-bound condition) he enters the factory with four other children. Wonka reveals to the children (and their parents) his world of pure imagination inside the factory walls including the Oompa Loompa creatures that help him create his chocolate products. The reactions we see of the cast as Wonka (played here by Gene Wilder) shows them the factory is actually genuine surprise (i.e. not entirely acted) as none of them up to this point had actually seen what the production team had created. Over the course of the rest of the film the children encounter the wonderful (and dangerous!) world that Wonka has created and managed for most of his adult life. 

Dahl himself disliked this portrayal of Wonka, with one biography stating “He had serious reservations about Gene Wilder’s performance as Wonka, which he thought ‘pretentious’ and insufficiently ‘gay [in the old-fashioned sense of the word] and bouncy.'” The film is notoriously dark and Wilder is quite chilling at times. One by one the children prove themselves to be awful in one way or another and meet grisly ends until we are left with Charlie. At the end of the film Wonka asks Charlie what he thinks of the place and he says “I think it’s the most wonderful place in the whole world” to which Wonka replies “I’m very pleased to hear you sat that because I’m giving it to you”. Whilst he had punished the other children severely for their immorality, Charlie had lived up to his standards and was the kind of heir he wanted to continue his work at the factory. So the story was, for all intents and purposes, a rather macabre tale of succession planning through a string of child homicides. Incidentally, Dahl himself was in many ways as complex and multifaceted as Wonka. While many of his stories point towards kindness, empathy and a love for diversity he was by his own admissionan anti-Semite. Moreover, in earlier drafts of Charlie and the Chocolate Factory he had actually wanted Charlie to be a black boy but was talked out of it by his agent of the time – so hopefully any future adaptation will see Dahl’s original idea brought to life.

57. Jordan Belfort (The Wolf of Wall Street, 2014) 

“Let me tell you something. There’s no nobility in poverty. I’ve been a poor man, and I’ve been a rich man. And I choose rich every fucking time.”

Martin Scorsese’s The Wolf of Wall Street is rip-roaring, adrenaline fuelled movie set within the finance sector in the 1980s. We first meet Jordan Belfort (played by Leonardo DiCaprio) as a young salesman and soon find out he is the kind of guy who, as the saying goes, could sell ice to the Eskimos. After taking an entry-level position in a stock broking firm he quickly learns the ropes and goes on to found his own trading firm Stratton Oakmont. Together, with his team, he not only defrauds rich investors out of millions of dollars he creates a company that is filled with money-hungry, ruthless individuals intent on scamming and conniving their way towards extreme wealth. The culture that he presides over (and helps to shape) is the most hedonistic work environment imaginable (cocaine, hookers, orgies, parties with dwarf throwing, all within the workplace). As a manager and a leader, Belfort is revered and even loved by his staff, whom he addresses via microphone (as he did in real life) to get them in to the right mind-set and inspire them to what he sees as greatness. Employees, if they do well, are rewarded with obscene amounts of money but if they do poorly they are punished, through the usual ways but also some rather unusual ones such as one scene where an executive is seen eating a pet goldfish to punish what he saw as an uncommitted worker. 

The treatment of women in the film is particularly (and purposefully) grotesque, in an effort to reflect the way that Belfort considered women to be mere objects that he could pick up, use and put down again. On one occasion, they offer a woman ten thousand pounds to shave her head (which, given her situation, she enthusiastically agrees to) – a true story confirmed in business partner’s Donnie Pozuff’s memoir and something he said he was most ashamed of. One article written by Joanne Lipman around the time of the film’s release suggests that from her own experience of the finance sector in the 80s whilst parts of the film are exaggerated (orgies on the trading floor), other parts are accurate or are not wild enough. As she says, a “friend, who worked on an investment-bank trading floor, was so accustomed to strippers in the office that after a while, she didn’t even bother looking up when naked women began gyrating near her desk. For my part, I laughed off obscene remarks by sources; I figured they weren’t used to professional women, and this was just their pathetic attempt to make small talk….Ask any woman who worked around finance back then what she thought about sexual harassment, and her answer will likely be a shrug: “We called it going to work.”

In reality, Belfort is probably a much worse person than the film even portrays. Whilst in the film he is shown hitting his wife, in reality (according to his own memoir) he kicked his wife down the stairs while he was holding his daughter. He also recounts (graphically) how he sexually assaulted a stewardess on a plane and other instances that went even further than what Scorsese was willing to portray. The film, in many ways, needs you to root for Belfort rather than despise him so intentionally rows back from completely demonising the character. Whether this is a good thing or not is highly questionable. We are left with an incredibly entertaining film but Belfort has managed to capitalize greatly from its success, embarking on global speaking tours and selling his books and merchandise in higher numbers than ever before. There is apparently still an audience for this kind of highly masculine, forceful “seize the day by the balls” approach to management. In one negative review of his show in Dublin , it was said “there were at least five males for every female. Testosterone was at a premium. Lots of suits with pin stripes wide enough to accommodate a shoe. Lots of guys with shades pushed up onto foreheads. Lots of wannabe-wolves. Most of them looked to be under 40, with enough fuel in the tank to feed dreams of becoming overnight millionaires.” Belfort is a fascinating example of a boss being able to take a mythologized version of himself and turn that in to a money making machine – it seems that the man really can sell anything, including himself. 

58. Diana Christensen (Network, 1976) 

“I’ve been telling you people since I took this job six months ago that I want angry shows. I don’t want conventional programming on this network. I want counterculture, I want anti-establishment. I don’t want to play butch boss with you people, but when I took over this department, it had the worst programming record in television history. This network hasn’t one show in the top twenty. This network is an industry joke, and we’d better start putting together one winner for next September. I want a show developed based on the activities of a terrorist group, “Joseph Stalin and His Merry Band of Bolsheviks,” I want ideas from you people. This is what you’re paid for. And by the way, the next time I send an audience research report around, you’d all better read it, or I’ll sack the fucking lot of you. Is that clear?”

April 18th 1930 was a peculiar day in BBC news history. The people of Britain gathering around their wirelesses tuning in to the 20.45 evening bulletin would have been surprised to hear that “there is no news today”. Instead, piano music played for the remaining 15 minutes of the broadcast and then returned to broadcasting coverage of a Wagner opera. Today, in an era of pandemic and economic peril, a day without news (whilst sounding absolutely fantastic) seems absurd and ridiculous. News stalks us at every corner, on our TVs, on our smartphones and laptops, on radio or broadsheets, it is inescapable for more than a short period of time. The first film to predict this future with any kind of clarity was Sidney Lumet’s Oscar winning satire Network. It follows the fortunes of a fictional broadcasting network UBS. With ratings at an all-time low, the president of the Network news division, Max Schumacher, informs long-time anchor, Howard Beale, that he will no longer be hosting the nightly news show. The following evening Beale reveals on air that he is having to step down and that because of this he will commit suicide on next week’s show. He is momentarily fired for this outburst but after many apologies and reassurances he is allowed his final farewell. This leads to a huge ratings spike for his final show in which he launches in to a tirade against the whole news industry. Rather than let him leave after such a “successful” show, the corporation decide to let Beale stay, keeping his confrontational approach with the now infamous catchphrase “I’m mad as hell and I’m not gonna take this anymore!”

Diana Christensen (played by Faye Dunaway) is an ambitious programming executive who believes that she understands the formula required to win the ratings game. It requires a new approach that does away with the old rules of reporting bland news stories that few people are interested in. People, according to Christensen, want exciting, entertaining news that make them passionate – either for or against and which make them want to tune in next week (akin to a soap opera). With this in mind, she makes an agreement with a band of terrorists called the Ecumenical Liberation Army and creates a “news” docu-drama about their activities and begins to blur the boundaries between entertainment and news. She also gives Beale his own show and encourages him to push his angry-man character to its limits. Unfortunately, this runs out of steam and with his ratings declining and them unable to sack Beale, Christensen and other network executives hire somebody to kill Beale live on air – which in turn leads to ratings spike in the coverage of his killing. Based on broadcasting executive Lin Bolen (who was the first female Vice-president of programming at a TV network) Christensen encapsulates the obsession with ratings that grew steadily through the nineteen seventies. Bolen stated on the year of the film’s release (1976) that “the ratings game is at its zenith. The numbers have never meant more than they do this year.” 

Christensen is especially fascinating as an onscreen boss as she breaks with convention but it is with the conventions of news rather than her gender. Whilst many portrayals of women in the workplace at this time gravitated towards women proving themselves in the workplace, this is never even in question for Christensen (see this clip of her in the office in total command of the situation). She belongs there, even more so than any of the male characters in the film, because she understands the game better than anybody else. The rest of the staff are clueless in comparison. Towards the end of the film, Schumacher (her boss and now ex-lover) says “You are television incarnate, Diana…indifferent to suffering, insensitive to joy. All of life is reduced to the common rubble of banality.” Schumacher may reveal some truth in what he says about Christensen, but in doing so he reveals just as much about himself. It is he who is not up to the job and Christensen who has the fearlessness and bloody mindedness to succeed where he has failed.  

It has been suggested that Network (through Christensen) invented ‘reality TV’ and it was certainly prescient of the emergence of 24 hour news (and the need to create ‘fake’ news). Indeed it foreshadows the Trumpian approach to politics and shock jock tactics employed by news readers like Bill O’ Reilly and Sean Hannity on FOX News or more recently in the UK, Piers Morgan on Good Morning Britain or Nigel Farage/James O’ Brien on LBC Radio. In the years after the film “I’m mad as hell and I’m not going to take it anymore!” was used regularly in popular culture and is still a relatively well known catchphrase today, 40 years later. As Faye Dunaway writes in her autobiography ‘there was a great disillusionment and a growing sense that television was a part of the unravelling of the nation in some strange way that people could not quite fathom or articulate. Network was truly art predicting life.’ It continues to predict with frightening accuracy. 

59. Roger Sterling (Mad Men, 2007) 

“Well, I gotta go learn a bunch of people’s names before I fire them” 

In order to be a successful renegade manager you need to have one of two things, or ideally both. First you can be a genius in your field (a la Mark Zuckerberg) so that when you diverge from the usual playbook people follow you regardless. They assume that you have seen what others cannot. Alternatively you can have charm. So that you can convince others that you can see what others cannot and have the capacity to make them believe you (even if sometimes you are winging it or bullshitting). Roger Sterling, in AMC’s Mad Men, falls in to the second of these categories. Mad Men is a drama set in the 1950s/60s following the lives and back stories of a group of advertising men, their families and secretaries. Sterling (played by John Slattery) is senior partner at SCDP has a way with words as a manager that enables him to get away with more or less anything. He walks around the office (as was common at the time) with a glass of Scotch, jokes constantly about their business dealings and spends much of his time flirting with much younger secretaries, one of whom he makes his second wife.  We learn over time that Sterling was once a naval officer in World War 2 and much of his cavalier attitude probably comes from the fact that all the trauma and death he saw during that period makes life in the office so much less significant. He is so much of a loose cannon that when dealing with one of their new partners, Japanese firm Honda, Sterling (who is known to despise the Japanese because of his encounters with them in the war) is kept as far away from the deal as possible. Renegade bosses can be helpful at times when trying to innovate and find new ways of working, but when it comes to stability, they tend to not be the most reliable of individuals.

60. Annalise Keating (How to get Away with Murder, 2014) 

“Think carefully, everything after this moment will not only determine your career but life. You can spend it in a corporate office drafting contracts and hitting on chubby paralegals before finally putting a gun in your mouth or you can join my firm and become someone you actually like. So decide: do you want the job or not?”

The anti-hero is perhaps the central defining feature of the golden era of television we have experienced over the past 25 years. The blurring of the boundaries of bad and good in which slick and sophisticated writing makes us sympathise with and support a character that shows characteristics not traditionally attributable to a hero. At first, we predominantly saw the emergence of white male, middle aged anti-heroes, in the form of tyrannical mob bosses (Tony Soprano – explored here at number 60), lecherous but charming advertising men (Don Draper, entry 82) or meth dealing chemistry teachers (in AMC’s Breaking Bad) that we that we felt genuinely sympathetic towards and cheered on. Occasionally (but much less often) the anti-hero has been a white woman in the form of, say, renegade lawyers (see Patty Hewes in the next entry) or soviet double agent spies (Elizabeth Jenning’s in FX’s The Americans) but even this is a much more difficult task to pull off for a writer of a TV show or movie because of well documented culturally ingrained views on what we expect from women when we see them on the screens. It had been considered more risky to have women behaving badly on our screens because it was assumed or feared that the audience simply weren’t ready for it – and the producers were less ready to take a risk. All of this was quite obviously also ingrained in an extremely patriarchal, conservative vision that still remains at least partially ingrained in TV and film.  Even more rarely, however, has there been a depiction of a black female antihero on our screens. Thankfully, this is quickly changing and one of the more recent depictions is that of Annalise Keating played by Oscar winning actress Viola Davis. 

Keating is a leading criminal defence lawyer and professor (yes somehow she manages to do both roles, it’s a TV show). In her role within the University she teaches her class “How to get away with murder” as a way of introducing her students to the various ways clients might be able to create reasonable doubt within the minds of juries and therefore emulate her career. She chooses five students that she sees most promise in to join and work under her within her law firm (so in this sense she manages them!) in actual cases. One case in particular becomes the focus of the show in the first season: the disappearance of a young girl on campus, that the students themselves to varying degrees are mysteriously aware of. On one level the TV show explores the moral murkiness of being a defence lawyer – of trying to get a cold-blooded killer or a child rapist away from imprisonment whilst also trying to retain a sense of right and wrong. On a more individual level, we are introduced at first to a hard edged, frightening, potentially amoral side of Keating and only slowly learn about the other sides of her as the show progresses as we learn about the sensitive, abused, emotionally destroyed aspects of her character. Keating provides us with one of the most multi-dimensional characters in TV history, as we are left wondering exactly what this woman is capable of (committing murder herself?) but also what might have led to her becoming this person in the first place. 

The depiction of this multi-dimensional character in a leading role, managing others who are relying her to teach them and to guide them is as many others have said ground breaking in its content. The sheer complexity of the character was groundbreaking in and of itself, but black women have tended to not get these roles. Even Davis, herself, suggested in arecent interview about the show: “It’s changed the course of my career and it’s shifted my life in a way. I mean, I stepped into a character that I thought very much I was not born to play. I just thought, you know, this is not a role that I would be the first actress that would come to your mind,” Thankfully, she was and the rest is TV history. We can only hope that this role has smashed down doors and broken misguided (and let’s face it racist) assumptions about what parts black women can and cannot play. Keating is about as multi-dimensional as a manager you are likely to find in TV and film. As she says towards the end of the programme to a jury: “Who I am is a 53-year old woman from Memphis, Tennessee named Anna Mae Harkness. I’m ambitious, black, bisexual, angry, sad, strong, sensitive, scared, fierce, talented, exhausted – and I am at your mercy.” Hopefully depictions of strong, black female women in roles can in some small way begin to shatter wider social prejudices that we know hold back black women from and within managerial roles. In this sense TV and film might be able to play a role in helping to shatter illusions about identity that have been built up over many decades and indeed centuries and help young women to create see the possibilities of new identities that are rich, complex and challenging. 

61. Patty Hewes (Damages, 2007) 

“All of you are members of an extraordinary team, and I value each and every one of you. If you want to quit, just tell me now. But if you call in sick Thursday or Friday, don’t bother coming in Monday. Your jobs won’t be waiting for you. That grenade was never meant to destroy our office. It was meant to destroy our resolve.”

Patty Hewes (played by Glenn Close) is a top-notch prosecution lawyer who runs a firm that has made it their business to take on high profile clients who are abusing their positions of power. This includes, for instance, billionaires that abuse their employees, pharmaceutical companies that run dangerous drug trials in efforts of making profits, stockbrokers committing insider trading etc. So far, so good. These are people that most decent human beings would find pretty dislikeable. However, the twist of the show is that Hewes is pretty much willing to go to any lengths as a boss with her team to prosecute these individuals whether she has the evidence or not, whether this means bending the law, manipulation, bribery and at times, even more serious measures. Whereas Annalise Keating in the previous entry was ground breaking as an antihero due to her skin colour, it has been argued that Close’s portrayal of Hewes is as much because she is a strong, fit and powerful older woman. Out of the window goes the stereotypical weak or mothering characteristics of older women and here we have a woman using every moment of her experience to dominate (predominantly) men in ruthless ways in boardroom settings and corporate law. Has been compared to Lady Macbeth in terms of her ruthlessness and her desire to come to terms and own her role as a woman in a predominantly male world. 

A fascinating aspect of this renegade managerial identity however, is how (and even whether) it is able to combine the good and bad parts of the characteristics at play. It is a constant balancing act for the writer in TV and film but one suspects for anybody adopting such an identity in the workplace. How far can a person push the limits without becoming totally unlikeable and destroying sympathy for themselves? How far can a person push it in terms of being nice without destroying the fearful image they have cultivated? This goes back and forth constantly. As Close said in an interviewabout her role: “I don’t think I’m playing an evil character; evil’s a strong word. Manipulative? Yes. Wanting to win? Yes….She is an incredibly delicious character and I think the fascination with her – and what I like about her – is that as devious as she can be, she is still a kind of role model because she is in control of her own destiny. She’s at the top of her profession and takes no prisoners. I think what also draws people in to her is there are so many secrets. She has a very, very private side.” It is this private side that many renegades need to keep a secret – as once people fully know and understand the soft underbelly of a character like this it is impossible to maintain the façade. Despite this however, one of the people who knows her best, Glenn Close, said in a recent  interview that whilst she loves the character, “[she] would be a bit intimidated by her if [she] had to walk in to her office”. That goes for two of us! 

62. Griffin Mill (The Player, 1992) 

“I was just thinking what an interesting concept it is to eliminate the writer from the artistic process. If we could just get rid of these actors and directors, maybe we’ve got something here.”

The late, great film reviewer Roger Ebert described Robert Altman’s The Player as a film “about an industry that is run like an exclusive rich boy’s school, where all the kids are spoiled and most of them have ended up here because nobody else could stand them. Griffin is capable of humiliating a waiter who brings him the wrong mineral water. He is capable of murder. He is not capable of making a movie, but if a movie is going to be made, it has to get past him first.” Mill is a Hollywood executive who spends his days listening to other people (directors, producers) pitch film ideas to him and he decides whether to give money to make the film or not – an ideal job. However, things take a turn for the worse when he receives a postcard threatening his life. 

The rest of the film follows his attempts to understand what exactly is going on and the mysteries that surround the predicament he finds himself. He is essentially a boss that will stop at nothing to hear a good story and this leads him to a morally murky world that we call Hollywood. The film has been celebrated as a sharp satirical look at what goes on in modern Tinseltown now that the true “great” studio executives (the likes of Daryl Zanuck, David O. Selznick) have died and given way to a new, very different, managerial generation. As Ebert says in his review these new executives “no longer seem to have the power to perform miracles. The new gods are like Griffin Mill — sleek, expensively dressed, noncommittal, protecting their backsides. Their careers are a study in crisis control. If they do nothing wrong, they can hardly be fired just because they never do anything right.” In The Player, Mill almost creates a crisis and turns himself in to a temporary renegade in order to invent a story that might be different to the frankly awful pitches he had been receiving. In this sense, the renegade bosses can be born just as much out of boredom than of madness, and sometimes there is a thin line between those two things. 

Identity Seven: The Burdened Boss 

We often think of bosses as all-powerful individuals. In controlling the allocation and flow of work, hiring and firing and determining the strategy of the organization they have considerable decision making autonomy. We therefore tend to assume that this autonomy will lead them to be happier working individuals – certainly happier than the workers at the bottom of the hierarchy. This is obviously not always the case. The false assumption here is that a) managers actually have the freedom to make the decisions they want to make and b) that when they do have this freedom, it is an enjoyable experience wielding power over others. In reality, the reported high levels of stress in managerial positions – usually due to heavy workload, and the pressure of being in charge – can lead some managers to feel overburdened and/or unfulfilled in their roles. Rather than feeling empowered and liberated at the top of the hierarchy, they can feel isolated, lost and alone. My colleague Professor Nancy Harding writes wonderfully about the contradictory feelings experienced by managers, insofar that they can simultaneously feel pleasure at being in positions of power but guilt for having this power over others, making decisions that impact their lives and well-being greatly. The manager is essentially a powerful figure that is also very often quite powerless to escape the difficulties of their role. The portrayal of the burdened boss in TV and film is rich and complex therefore, and provides a fascinating insight in to the paradoxical and conflicted nature of managerial identity. Here are some of the best examples of this type of boss in fiction:

63. Reginald Perrin (The Fall and Rise of Reginald Perrin, 1976)  

“Here lies Reginald Lolanthe Perrin. He didn’t know the names of the trees and the flowers, but he know the rhubarb crumble sales figures for Schleswig-Holstein” 

Monotony is one of the biggest burdens faced by bosses in their working lives. It is easy to imagine a real sense of repetition being experienced if every day a boss is faced similar issues, with similar solutions and similar challenges and obstacles. It might after a while lead a manager to question: is this all there is to life? Is this really who I am? Reginald Perrin (played by Leonard Rossiter) is a classic British sitcom character that embodies this kind of internal struggle played out within a manager’s everyday life. Perrin is a middle-manager who is going through a mid-life crisis. He spends his days fantasising about escaping his job  or having an affair with his secretary – anything that does not involve his mundane managerial tasks. Perrin decides to fake his own death but after spending time trying to find a new role in life realises that he misses his wife. He returns to his own workplace only to find that nobody has even noticed he had even left in the first place. Bored again with his role within the company he leaves to set up his own business, Grot, which despite every effort to make it fail (including hiring seemingly terrible employees) it succeeds regardless. In one famous scene, the board room (one might just easily write “the bored” room!), he asks his hapless employees to pitch ideas, which they do. Convinced they are ridiculous ideas he launches them only to see Grot’s share price rocket. Bored again, he eventually leaves the company to embark on a life outside of the managerial sphere. 

On his influence for the characters in his original novel, writer David Nobbs said: “My train was always teeming with commuters and I spent the journey watching everyone with their briefcases, rolled umbrellas and bowler hats heading for the office. Even at that young age, I hoped I’d never end up like them.” This is one of the most bizarre things about management, particularly as so many young adults now enter business school’s each year aspiring to become managers. Perhaps there is an expectation that being within this role will be exciting and rewarding and perhaps this will be the case for some people as they climb the corporate ladder. However, for some, there will undoubtedly be an overwhelming experience of disappointment with the repetitive nature of being a boss. 

64. Charles Foster Kane (Citizen Kane, 1941) 

Charles Foster Kane: You know, Mr. Bernstein, if I hadn’t been very rich I may have been a really great man.”

Walter Parks Thatcher: Don’t you think you are?”

Charles Foster Kane: I think I did pretty well under the circumstances”

One of the strangest burdens a boss might face within his work is that of success. What happens when you are an incredibly successful business man for instance, but you remain empty and unfulfilled? What happens when you reach all of your goals, you reach the top of the summit, but the view is not what quite as exhilarating or rewarding as you expected? This is one of the key themes of Orson Welles’ Citizen Kane in which he plays the titular character Charles Foster Kane. In the opening scene, we witness Kane’s death as he famously drops the snow globe and utters his final enigmatic words “rosebud”. We are then taken through flashbacks on a journey through Kane’s life. We see him playing happily as a child in the snow on his new sled but then being sent away at the tender age of 8 to live with his guardian Thatcher, a rich banker who attempts to educate him in the ways of the world until he receives his huge inherited wealth in his mid-twenties. Kane never warms to Thatcher and when he buys and runs a newspaper he actively rebels against Thatcher’s and his own investment interests through various campaigns against slum landlords and monopolies in the railways amongst other things. In one fantastic scene Thatcher complains to Kane about these campaigns that are costing  not only him money but Kane himself as a key shareholder. In response to this tirade Kane speaks about “how to run a newspaper” and explains:

The trouble is, Mr. Thatcher, you don’t realize you’re talking to two people. As Charles Foster Kane, who owns eighty-two thousand, three hundred and sixty-four shares of Public Transit, preferred – you see, I do have a general idea of my holdings – I sympathize with you. Charles Foster Kane is a scoundrel, his paper should be run out of town; a committee should be formed to boycott him. You may, if you can form such a committee, put me down for a contribution of one thousand dollars. On the other hand, I am the publisher of the Inquirer! As such, it is my duty – and I’ll let you in on a little secret, it’s also my pleasure – to see to it that the decent, hard-working people in this community aren’t robbed blind by a pack of money-mad pirates just because – they haven’t anybody to look after their interests. I’ll let you in on another little secret, Mr. Thatcher. I think I’m the one to do it; you see, I have money and property. If I don’t look after the interests of the underprivileged, maybe somebody else will – maybe somebody without any money or property – and that would be too bad…

We see the inherent good of Charles Foster Kane in these moments but ultimately it proves unfulfilling and he also fabricates news stories to encourage wars and such in ways that later weigh down upon his conscience. We witness him trying to find happiness through attempts to enter the political sphere and within his love life but ultimately he remains unfulfilled and dies uttering those seemingly strange words “rosebud”. As his mansion is being cleared out, we see staff burning what they consider to be old and useless things including the toy sled that he was given by his parents as a child. As the camera pans round we see the word “rosebud” written on the side of the sled. We learn that this word reflects his lost childhood and a simpler time before the responsibility of the world of money and management and power subsumed him and he lost a life which he could have potentially lived. It is a burden he carries sadly throughout his whole life and which weighs heavily upon him and in that moment we feel we understand him and his life experiences on a much deeper level. 

It is widely believed that Kane was based on the real-life newspaper tycoon William Randolph Hearst, whose life has many things in common with the character. Rather incredibly, Welles was only 26 years old when he wrote and directed Citizen Kane. In one frankly wonderful interview with him talking about how he made the film he describes how the Hearst family actively tried to block the film from being distributed and how Hearst himself turned down a personal invitation to attend the film’s opening. Welles suggests that that was one of the key differences between Hearst and Kane: Kane had a lot more class and would have come to the opening night. Perhaps his is the real-life burden of being a rich tycoon, – you have interests and advisors and forces that seem beyond your control, ushering you on with a life that you never asked for or even desired. These are ultimately invisible managerial burdens of expectations and disempowerment that shape and influence identities in profound ways but which in reality outside of TV and film usually go untold.

65. George Wade (Two Weeks Notice, 2002) 

“When I say I’m poor, I mean we may have to share a helicopter with another family.”

A running theme within this sub-section on burdened boss could be captured by a continuing desire within many TV shows and films for us to have sympathy for billionaire CEOs (see entries 64 to 68 inclusive!). That they might be rich and in powerful positions but that ultimately they are lost and sad and unfulfilled. In the current economic climate this is an incredibly difficult task. Whilst a film like Citizen Kane can (through remarkably good writing and direction) achieve this, it is slightly more challenging to buy-in to within a standard rom-com format. Nevertheless, George Wade (played by Hugh Grant) in Two Weeks Notice is one of the stronger attempts at doing this, providing us with a playboy Billionaire owner and CEO of a real estate empire that despite all of his success is well and truly lost and naïve. In to his life walks Lucy Kelson (played by Sandra Bullock) who is the complete opposite – a principled, kind, intelligent lawyer who specializes in environmental law and historical preservation. Her main goal is to save the local community centre. Wade agrees to help with this so long as she works for him. Before long, she is not only acting as his aide but also changing him on a much deeper level, helping him to realise just how unsatisfied and lost he feels with his currently empty existence. Wade is ultimately burdened insofar that he has become lost within a world of greed and in doing so lost sight of who he actually wants to be. This is a more light-hearted take on the soulless-ness of managerial practice and falls in to the somewhat outdated vision that what every lost man(ager) needs is a woman to save and reform them in to something better. On the other hand, the film is an interesting cultural reflection of these kinds of assumptions that go on within the male fantasy of being rescued and reformed and ultimately to be made a better man at the hand of a compliant and caring woman. 

66. Edward Lewis (Pretty Woman, 1990)

Vivian: that would make you a…lawyer.

Edward Lewis: what makes you think I’m a lawyer?

Vivian: You have that sharp useless look about you

Pretty Woman inhabits a complex place in the psyche of the modern audience.  If you were told the plot of the film with absolutely no knowledge of the actors or the tone of what’s involved – business man meets prostitute, business man throws money at prostitute, they fall madly in love and they live happily ever after – it might seem a little difficult to see the charm of the film. And yet, the film is every bit as wonderful today as it was when I first watched it as a teenager in the early 90s. Edward Lewis is CEO of Edward Lewis Enterprises, a company that carries out leveraged buy-outs of struggling firms that it can buy, break up and sell on for a large profit. Indeed, we learn that the third company Edward ever ‘broke up’ was his own father’s. He is a ruthless man. After meeting Vivian, the care-free, smart, honest prostitute and offering her $3000 to spend the week with him he (rather harshly) says to her: “You and I are such similar creatures Vivian. We both screw people for money”. Whereas Vivian’s burden is a lot more simplistically that of poverty and needing to pay her rent, Edward’s burden carried throughout the film is one of guilt and perhaps even more so a lack of fulfilment in life – as we know his dealings are far from ethical or rewarding – but that his job leaves him feeling empty and alone. So much so that he has to pay women for their company. In this sense he is a much more tragic figure than the woman who accompanies him – he has less grace and less decency (to begin with) than Vivian has in her profession. And this one of the central reasons why the film works. 

Nevertheless, in the #metoo era the film has been criticised as extremely outdated. Gere himself has said in one interview that the film was a “silly romantic comedy” and whilst people ask him about it a lot that he has “forgotten it.” He suggested that rather than being a romantic gem it glorifies greedy and selfish Wall Street types: “It made those guys seem dashing, which was so wrong…thankfully, today, we are all more sceptical of those guys.” It is true that Edward appears especially aloof and condescending at times, and the sexual assault scene (in which one of Edward’s colleagues, Philip, tries to rape Vivian) is handled in a way which focusses on the now destroyed business relationship between Edward and Philip (rather than the actual attempted rape). In addition, whereas the awful aspects of Edward’s profession are there for all to see, Vivian’s involvement in her profession is played down somewhat. We are ensured to know that Vivian is new to the sex trade and doesn’t do drugs – this is used to purposefully soften the edges of her involvement in the profession. And yet, somehow, despite all of this the film does retain its appeal to many of us. For instance, one article (published in The Guardian) on the thirtieth anniversary of the film suggested, “there’s every reason to resist the gross materialism and conservative sexual politics of Pretty Woman, but Roberts makes Vivian’s ascendance to the upper crust a victory for the little guy. Being happy for her is as easy as being happy for a friend who hit the lottery.” However, the fact that Lewis has probably finished his day at work and slept with dozens of prostitutes before he settles with Vivian is understandably something that the director does not wish to dwell on too much within the film. It might ruin the magic somewhat. We hear that he usually has a different woman on his arm at various events and yet many of us are still drawn in to the charm of the relationship. It helps that Gere is impossibly good looking in the film – how might it change the story if for instance, it was a regular overweight businessman, red faced and sweat-ily doling out money to a prostitute, paying to win her affection? It would be an interesting option for Pretty Woman 2 but in all seriousness I suspect we will never know. Sometimes the fairy tale is more comforting to watch than the stark reality of loneliness, desperation and exploitation within the boardroom and on the streets. 

67. Nicholas Van Orton (The Game, 1997) 

“And you really believe that just because you publish children’s books, people are going to care about my reputation? You can have pictures of me wearing nipple rings, butt-fucking Captain Kangaroo. The only thing they care about is the stock and whether that stock is up or down!”

The Game rests on what central premise: “What do you get for the man who has everything?” These are words are spoken by Conrad Van Orton as he hands him his birthday present at lunch to his brother, Nicholas Van Orton (played by Michael Douglas). The latter is an obscenely wealthy investment boss and has everything money can buy, but his life (as noticed by his brother) is empty aside from that – he is single, miserable within his work and haunted by witnessing his father commit suicide on his own 48th birthday many years ago. He feels the weight of his own personal history upon him as he has hit the same age and feels incredibly unrewarded by his profession. The present that Conrad gives his brother is a voucher to play a game run by a company called Consumer Recreation Services; a game that he feels will revitalise Nicholas and change his entire life. The film follows Nicholas as he embarks on a ‘game’ that spirals out of control to see him lose his job, his home, his reputation and his dignity. The important question you ponder throughout this Hitchcockian film is: is this really still a game? And, perhaps most importantly, what is the actual point of the game if it is? In many respects, the film is about shattering a managerial identity in order to put it back together again.

68. Bruce Wayne (Batman Begins, 2005)  

“I, uh…I wanna thank you all for coming here tonight and drinking all of my booze. No really. Uh…There’s a thing about being a Wayne that…you’re never short of a few freeloaders, like yourselves, to fill up your mansion with, so, here’s to you people. Thank you. Mm…I’m not finished. To all of you, uh, all you phonies, all of you two-faced friends, you sycophantic suck-ups who smile through your teeth at me, please leave me in peace. Please go. Stop smiling. It’s not a joke. Please leave. The party’s over. Get out.”

Bruce Wayne (played by Christian Bale) has a rather peculiar burden which he carries as owner of Wayne Enterprises: he is not who he says he is. Yes, he is Batman – The Dark Knight – the protector of Gotham City, but he is also pretending in his everyday life within the hugely profitable organization which he inherited from his deceased parents. Wayne deflects suspicion from his heroic role in wider society by embracing all the worst characteristics of a billionaire owner – he is brash, rude, cocky and a playboy, flaunting his wealth with expensive cars and multiple women on his arms. In many respects, Batman is closer to who he really is as a person and Bruce Wayne is his alter ego used to sustain the noble lie. The day-to-day running of Wayne Enterprises is left to Lucian Fox, Wayne’s trusted friend who ensures that the organization is run correctly. In some Batman comics, Bruce is forced to take a more active CEO role within Wayne Enterprises. For instance, in No Man’s Land following an earthquake in which the company is one of the few buildings left standing Bruce takes full control to try and invest in small businesses and save Gotham City. For once Batman was powerless and the need was to focus on more capitalist means to get people back on their feet. However, for the most part, the CEO position is a mask and a burden in-and-of-itself – he gets no praise and recognition for the good work he does as the caped crusader and most people think Wayne is not much more than a spoilt and damaged offspring of a man and woman who did such good things for the city. Not getting recognition for the full extent of actions as a manager (and people focussing merely on negatives) can indeed be a heavy burden to carry. 

69. Jules Ostin (The Intern, 2015)  

“Mark Zuckerberg never brought in a CEO – and he was a teenager!”

It is telling that only one woman appears in this sub-section on burdened managers. Perhaps the cultural perception being reflected through TV and film is that women are not portrayed as burdened as managers because they are often (wrongly!) considered as merely happy to be in such a role in the first place. Jules Ostin (played by Anne Hathaway) is CEO and founder of an e-commerce fashion start-up that takes part in a community outreach project involving hiring senior citizens to the organization. In walks Ben (played by Robert De Niro) who is hired to work alongside Jules which he takes extremely seriously, going above and beyond to play an almost fatherly role within the organization. Due to the heavy demands of the job (and her difficult family life) Jules becomes increasingly under pressure from the board  to bring in an outside CEO who they believe will be able to work more hours and do a better job. Jules, feeling attacked by such a suggestion, feels the heavy burden of expectation and unrecognised effort particularly as a woman founder. She initially decides to give in to pressure to hire an outside CEO and focus on her family, but ultimately decides to stay on in the position after being reminded of her multiple strengths and how much she enjoys the job. The film’s portrayal of Ostin has been praised as a role model for women in organizations and the pressures that they might experience in trying to run their own business.

70. Tony Soprano (The Sopranos, 1999)  

“We’re soldiers. Soldiers don’t go to hell. It’s war. Soldiers kill other soldiers. We’re in a situation where everyone involved knows the stakes and if you are going to accept those stakes, you’ve got to do certain things. It’s business.”

The Sopranos is regularly voted the greatest show in television history and is widely regarded as the beginning of the third golden era of TV. Tony Soprano (played by James Gandolfini) is a New Jersey mafia boss who is loosely based uponreal life crime boss Vincent “Vinny Ocean” Palermo. However, this is no ordinary, cliched representation of a mob boss. The show primarily explores the burdens and difficulties of being in charge of a criminal organization, having to be a sociopathic, ruthless killer to maintain control whilst also ensuring your kids go to school on time, that your wife remains happy and, of course, that your mistresses do too. In the pilot episode we witness Tony having a panic attack for the first time as all of the pressures of life descend upon him and he finds himself in hospital, at first thinking he is seriously ill. Instead, he is told to go for counselling, and much of the strongest parts of the show are us listening to Tony talk to his therapist Dr Melfi, who he is resistant to at first but who he increasingly trusts to unload upon the difficulties that he is encountering in running a profitable violent enterprise, murdering friends and foes and occasionally even family. 

As Tony says in one episode: “You think it’s easy being the boss?” It sure as hell isn’t and we get an inside view of just how difficult life can be. Usually in TV and film the crime boss is depicted as a glamorised position in which the boss sits back and enjoys the spoils of war whilst his lieutenants get their hands dirty – this portrayal within The Sopranossuggests something entirely different. We see instead that it is lonely and scary at the top, but there is absolutely no way that you can let anybody else know this, or risk losing your position entirely. The therapist in the show is almost like a form of confession for Tony, in which he can at times unburden himself and temporarily at least talk about just how difficult his role is. This reflects a much wider fear amongst those at the top of organizations of looking weak at any point. There is a machismo and masculinist desire to be seen as untouched and untouchable, of being someone without emotional distress or difficulty. Rarely, of course, is this the case. Interestingly, Gandolfini himself suffered significantburdens of his own playing Tony Soprano, becoming angrier in real life as he at times at least became more like his on screen persona. In some scenes he even placed a rock in his shoe when filming to legitimately annoy and frustrate him so his reactions had an added layer of authenticity. The frustrations of being boss in such a high pressured environment are only known to a small number of people (none of which I envy!), but The Sopranos offered us a deep and rich character study of what this might look like. It seems that even sociopaths carry burdens and fears, and this gave all of us watching a sense of security that if a man so tough and terrifying had mental health problems, maybe it was okay for us to have them too. 

71. Bank Manager (Fleabag, 2016) 

“They keep asking me, “What do you want from this workshop? “What do you want?” I’m not telling them what I want… I want to move back home… I want to hug my wife… Protect my children, protect my daughter. I want to move on. I want to apologise… To everyone… Want to go to the theatre… I want to take clean cups out of the dishwasher and put them in the cupboard at home…… and the next morning, I want to watch my wife drink from them. And I want to make her feel good. I want to make her orgasm again… And again.”

Inspired by Phoebe Waller-Bridge’s one-woman show, the full length sitcom is the best and indeed funniest piece of British television I have seen over the past thirty years. The bank manager (played by Hugh Dennis) is a small but perfectly formed character that the titular character encounters in her everyday encounters as a thirty-something woman living in London. Fleabag initially encounters the bank manager when asking for a loan which he turns down after she accidentally flashes him leaving him so mortified that in a moment of PC madness he feels obliged to turn her down for fear of appearing complicit in the act. Ultimately, the bank manager is burdened by his place in a world that he no longer understands and feels incredibly scared at acting inappropriately. In doing so, he has become paralysed by his fear and we learn that his home life has suffered immeasurably as well. The monologue above written by Waller-Bridger and delivered by Dennis with such delicacy and sadness reflects the sheer tragic nature of the boss’s situation. 

72. Ryan Bingham (Up in the Air, 2009) 

“Tonight most people will be welcomed home by jumping dogs and squealing kids, their spouses will ask about their day, tonight they’ll sleep, the stars will wheel forth from their daytime hiding places and one of those lights slightly brighter than the rest will be my wing-tail passing over.”

Another potential burden that faces many senior executives – before the pandemic at least – Is that of constant international travel. There are, of course, obvious attractions of this, escaping to interesting locations and being pampered in business class are hardly grounds for huge waves of sympathy. However, for many individuals being away from family and only seeing the inside of airports, taxis and hotel lobbies is hardly an exciting existence. Not so it seems for our next film character, Ryan Bingham (played by George Clooney), who seemingly adores jetting around the world in the pursuit of his profession. Bingham is a corporate downsizing expert for the Career Transitions Corporation. In short, when your employer is too scared to lay off its employees they call in Bingham and he flies in to do the dirty work, sort out a severance package and fly back out as soon as its agreed. We are told by Bingham that: “Last year, I spent 322 days on the road, which means I had to spend 43 miserable days at home.” A life of hotel bars, upgraded rooms and casual hook-ups that apparently keep him happy as he jets around the world. Aiming for his 10 millionth frequent flier air mile so that he will be promoted to lifetime executive flier and get his name on the side of a plane. 

And yet, we keep asking ourselves as we watch him fly from city to city: is he really happy with this kind of existence? He tells everybody he is and indeed encourages others to let go of their emotional and physical ties in motivational talksthat ask participants, “what’s in your backpack?” i.e. what physical and emotional ties to do we carry around that weigh us down and stop us from acting independently and freely. Bingham says: “make no mistakes your relationships are the heaviest components in your life…you don’t need to carry all that weight.” For anybody who is a social creature and relies and revels in the company of others this kind of assertion seems nonsensical. It is this weight which keeps us grounded. The social ties around us make us feel safe and anchored so that we do not get “carried away” or find ourselves “up in the air” metaphorically speaking of course. There is no reason to doubt that what Bingham is saying is something that he believes. He appears on the surface to be happy with his lonely existence of casual pick up and put down relationships, tethered to no-one and no-thing. This inability and lack of desire even to sustain social ties may be the burden in and of itself which he carries much to the shock and dismay of those around him. It is extremely easy for executives being asked to travel regularly in this way to lose social connections and slip in to a world where nobody really matters very much at all. It is one thing to accept that somebody might be able to find themselves happy in such a situation but another thing entirely to believe that they should want to actively work towards it. 

Identity Eight: The Heroic Boss

Another strand of managerial identity dominant in the cultural narrative is that of the heroic boss. The boss (and it tends to be exclusively he rather than she in this case) is positioned as a figure that was sent here to rescue us from the difficulties of organizing. They tend to possess (or at least want to be seen as possessing) super-human qualities which help them to see what other people can’t in situations of crisis. The hero identity seeks to create a dependency of employee to manager, in which in every difficult decision and situation, they are known to have an answer. They are smooth talkers, well-presented and (at least want to be seen as) highly sexually attractive. As with all heroes they tend to have a tragic back story which drives them (perhaps they came from “nothing” , a broken home, or left school at 16 and still rose to the position of boss) – the important thing is that they became this all seeing, all knowing individual largely under their own steam. In the US, figures such as Rudy Giuliani cultivated an image of himself as a heroic manager as Mayor of New York after 9/11. While in the UK figures like Alan Sugar and Richard Branson have tried to cultivate this heroic manager identity, with the latter going so far as mixing his business successes with naked women hanging off his back as he kite surfs through the ocean. Like all heroes though, the heroic manager always has a “kryptonite” that is their fatal undoing. For Branson this has come quite recently through his initially terrible treatment of Virgin staff during the coronavirus crisis but as with a lot of heroic managers they tend to find a way out of the mess of their creation in the end. 

The management literature itself has tended to focus in more recent years on the post-heroic manager, noting the problems inherent to becoming over-reliant on one individual. Nevertheless, the power of the heroic manager within the cultural narrative is still extremely strong – there is a huge attraction to the kind of boss who does have all the answers, even if in reality these people are rare to non-existent. Here are ten of my favourite heroic bosses from TV and film:

 

73. Tony Stark (Iron Man, 2008)  

“Is it better to be feared or respected? I say, is it too much to ask for both?”

There is a common trope in comic book characters of being a billionaire CEO by day and a superhero (or supervillain) by night. We have already covered Bruce Wayne/Batman above but there are other notable examples including Britt Reid/the Green Hornet (who owns and runs The Daily Sentinel) and evil genius Lex Luther (owner and CEO of LexCorp). The most relevant example at the current time however – due to his central role in the biggest grossing movie of all time, Avengers: Endgame – is Tony Stark, otherwise known as Iron Man. Like Bruce Wayne, Stark uses his immense wealth inherited from his parents and his talent for invention and innovation to fight evil in various ways. However, unlike Bruce Wayne he actually is a brash, cocky, outspoken playboy that has no desire to hide his identity – indeed, he courts media attention at times and is happy with being considered the hero. Through Stark Enterprises he creates defensive and offensive weapons/robotics/satellites that are designed to protect the vulnerable and kill the bad guys – although, it obviously doesn’t always run so smoothly. Stark is positioned in the film(s) as a man learning how to become a hero and ultimately he demonstrates a selflessness and sacrifice within his role where he puts other people’s well-being above his own. This reflects a wider cultural assumption that top leaders/managers should be able to do what others simply cannot do or are not willing to do. The implication being that CEOs are a special breed that can push organizations and more generally human kind forwards in ways that normal people simply cannot. How true or accurate to life this is outside of a comic book/film format is another question entirely, but the fact that it appears so regularly as a consistent message is extremely interesting. If a CEO considers themselves heroic, special or “super” in various ways, exceptional even, they will probably begin to act in those ways, believing themselves to be above social norms. One need only look at the likes of Elon Musk to get a glimpse of genius unbound from usual social conventions. 

74. Roger O. Thornhill (North by Northwest, 1959) 

“Now you listen here, I’m an advertising man, not a red herring. I’ve got a job a secretary, a mother, two ex-wivers and several bartenders depending upon me, and I don’t intend to disappoint them all by getting myself ‘slightly’ killed”

Roger Thornhill (played by Cary Grant) is a New York advertising executive. Thornhill is obviously a highly successful executive, at least if his immaculate Savile Row tailored business suit, his monogrammed matchbooks and handkerchiefs, and his exceptionally suave, debonair manner are anything to go by. Indeed, Cary Grant’s Thornhill seems to fulfil every personal wish of the conventionally aspiring (male) executive. As Lesley Brill points out in a 1982 article

Roger Thornhill is the sort of man who thinks of the perfectly aimed reply immediately, not later while brushing his teeth before bed. Although he has the defects of an ordinary man, he is handsomer, wittier, ‘better tailored,’ and more persistent than an ordinary man could be…Taller than anyone else in the film, he is capable of such feats of strength as surviving uninjured a collision with a truck and holding Eve above a precipice with one hand while hanging on to a cliff face with the other – as Leonard deliberately stamps on his fingers. It is his persistence, above all, which raises him to heroic proportions. He never flags in his determination, never retreats in the face of fear, self-doubt, or exhaustion. This doggedness, as it has for romantic heroes since Odysseus, eventually rewards him with a wife and a return home.

At the start of North by Northwest we meet Thornhill talking with his secretary before he travels by taxi to the Plaza hotel for a business meeting. While waiting with corporate colleagues he is mistakenly identified as a George Kaplan by some menacing heavies; heavies who, it turns out, work for a mysterious organization trying to smuggle microfilm of government secrets out of the country. Kaplan, we also learn later, never existed. He was a persona created by a government intelligence organization as part of an attempt to foil the smugglers. Getting manhandled out of the hotel is the beginning of a series of absurdly unlikely but breathtakingly glamorous adventures for Thornhill that are very much akin to a (certain kind of man’s?) wish fulfilling dream. These include escaping from the New York Police after apparently murdering a high-ranking official at the United Nations Building, outrunning a low flying aeroplane and climbing across Mount Rushmore away from deadly assassins.  

On Thornhill goes (a mere advertising executive) behaving and acting convincingly like an international spy, heroically saving the day and, of course in the end, getting the girl. This sort of representation of an executive manager is nothing short of pure fantasy, designed for current and aspiring executives who, of course, love to imagine themselves as these heroic figures, capable of adapting and adjusting to any scenario that requires their quick thinking and wise actions. Today Thornhill is celebrated as the epitome of a cool, suave and sophisticated man, creating a blue-print or an origin story for a “type” of man that would follow in TV and film. Without him, who can say that the likes of James Bond or Mad Men’s Don Draper would even have been written in the same way? When we look back to the birth of the heroic manager in popular western culture, we can indeed look no further than Roger O. Thornhill.  

75. Jack Donaghy (30 Rock, 2006) 

“Come On, Lemon. What Do We Elites Do When We Screw Up? We Pretend It Never Happened And Give Ourselves A Giant Bonus.” 

Jack Donaghy (played by Alec Baldwin) is an NBC executive on the Emmy Award winning sitcom, 30 Rock. The show follows the lives of a comedy sketch show runner, Liz Lemon (played by Tina Fey) at a television network and all the difficulties she encounters. Donaghy is hired to the network and immediately takes Liz under his wing, advising ways in which she can improve the show and make it a bigger hit. Donaghy is an alpha male, slick, forceful and in terms of style, cut from the same cloth as the previous entry (Roger Thornhill). He has a suggestion and answer for every business need and is portrayed (for comedic affect) as a heroic boss that can be parachuted in to save the day. We even learn later in shows run that Donaghy has written a book: “Jack Attack: The Art of Aggression in Business”, reflecting the wealth of experience he has in successful executive positions. And he imparts that experience to Liz, who in turn meekly listens and learns from her mentor – much to a lot of feminist critique from reviewers (suggesting she is infantilized in her working life by Jack) but also people defending her role as well. Like many characters in this section, their actions and words of wisdom within the TV show or film have become lauded in popular culture, and (despite the true intentions of the writers) they have regardless become something of a role model for aspiring executives. One Washington Post articlepraises Donaghy’s management style as something we can all learn from. Nuggets such as “Take mentorship seriously”, “Have a career plan but don’t let it stifle you” are all taken as themes of Donaghy’s managerial approach that people can, if they so wish, learn from and adopt within their own careers. 

76. Boss Baby (The Boss Baby, 2017)

Tim: “We could share.” 

Boss Baby: “You obviously didn’t go to business school.”

I have written above and elsewhere about the consistent negative portrayal of managers in animations over the past hundred years. From Stromboli to Cruella de Vil, the manager is usually portrayed as somebody who is wicked, manipulative and cruel. So what could be more contrasting in a film, than to portray a boss (complete with suit and briefcase) as a seemingly innocent and cute new born baby? Here we find out, in an insightful and hilarious film which begins with Tim Templeton, a seven year old boy who is completely happy with being an only child within his family unit – he gets all the attention from his Mum and Dad and doesn’t want a single thing to change. When his parents ask him whether he is ready for a baby brother however, things begin to change rapidly. Tim acts as the narrator of the film and we see the world through his eyes – the new baby he imagines is a boss, that commands all of his parents attention, he tears them away from concentrating solely on him. Boss baby is totally in charge. In one extremely clever scene (borne out of Tim’s imagination) we see a baby factory where babies are passed along an assembly line and one by one their feet are tickled with a feather. If they laugh, they are deemed ‘normal’ babies ready for delivery, if they do not laugh they are deemed humourless and sent to “management” where the baby is given a briefcase, a suit etc and expected to manage the baby making process. On the day that his own baby brother comes home for the first time, it is a “boss baby” that he sees strutting up the drive way ready to take over his and his parents lives. 

Boss Baby (voiced again by Alec Baldwin in a role not a million miles away from the previous entry), displays all the characteristics of a top CEO. He is a ruthless, driven alpha male who takes power naps, runs victory laps and wants to be the best boss that he can be even in this environment. As he explains to Tim who asks who he is: 


Boss Baby: Let’s just say I’m the boss.
Tim: The boss? You’re a baby, you wear a diaper!

Boss Baby: Do you know who else wears diapers, astronauts and NASCAR drivers, that’s who. It’s called efficiency, Templeton. The average toddler spends what, forty-five hours a year on the potty. I’m the boss, I don’t have that kind of spare time.

Little by little the two brothers forge a bond and Tim is able to put his jealousy aside to fight against what Boss baby has identified as his moral enemy: the CEO of PuppyCo. It turns out that many parents have simply stopped having babies and are instead just having puppies. With a new puppy set to be unveiled by this mega-corporation, it was putting the very existence of babies in jeopardy. We are then taken on a hilarious trip through corporate HQ by Boss Baby and introduced to the whole hierarchy of babies who have upheld their place in society over centuries, all with their own specific way of managing the organization. Together the two boys work together to defeat PuppyCo and to restore order to the baby making production system and their own family unit.  The film goes to the heart of what it is to be a young child and to imagine not only what it is to have a new younger sibling but what management at such a tender age is imagined to be through Tim’s eyes. Management is seen as invasive, it steals time, it is rude, abrasive, but in this case (through Boss Baby) it can change the rules and sometimes (very occasionally!) stop other worse meglo-maniacal bosses from doing even worse. 

A few of the lazier and immediate reviews of The Boss Baby implied that the baby was an infant Donald Trump and indeed, an intentional attempt at lampooning the newly elected president of the time. A closer viewing of the film however, recognises as Vanity Fair did that “This [baby’s] level of competence makes it abundantly clear: this really isn’t a Trump parody at all”. Indeed, Boss Baby is far too much of a renegade and a successful renegade(!) in management to be considered a lampoon of the president – however, the fact that the character touches on many of the clichés of a managerial figure (enough to provoke numerous articles making Trump-Boss Baby comparison) suggests that there is an underlying cultural understanding of top CEOs which homogenises them all in our eyes and in their own representation of themselves within wider society. CEOs are often impressions of impressions of CEOs gone before and the Boss Baby is a sort of cumulative mass of all these impressions over time which not only makes us laugh but makes us wince at just how incredible it is that many of these individuals play such a leading role within our most powerful organizations and institutions. If only a few more of the CEOs had the renegade and non-conformist but ultimately ethical nature that the young narrator Tim instils within his own little brother, then the world might indeed be a better place. 

77. Alan Shore (Boston Legal, 2004) 

“You have a job to do, and so do I. Yours is to sell socks and suspenders. Mine is to cross examine people like you and crush them.”

Managerial renegades within the workplace often (but not always) share two core characteristics. First, they tend to have a core morality about what is right and wrong but they are very capable of using unethical means to get there. In this sense they are not Kantian managers. They are Millian bosses. The ends justify the means to get the desired outcome. Second, they tend to use this approach to defend the underdog rather than those already in positions of power and influence. Alan Shore fits in to this bracket as a very successful corporate lawyer at Crane, Poole and Schmidt. He is willing to use blackmail, bribery and whatever it takes to win for his clients, who tend to be fighting to uphold liberal causes ranging from gun control to equal treatment within the workplace. In one episode Alan defends a young black girl who is refused the role of little orphan Annie on the basis that she had the wrong skin colour (and natural hair colour) for the role. Shore, against all of the odds, uses  his legal powers (and the girl’s incredible voice!) to convince the jury that she had wrongfully been denied the role. Whilst it was pitched/written as a purposefully over-the-top story at the time – an unwinnable case – it is amusing that ten years later Annie was actually played by a young black girl in the 2014 version of the film. A case of life imitating art. This entry might, indeed, be a slight cheat as whilst Shore is in a position of authority he is never technically promoted to partner of the firm. His actions make him at times seem untrustworthy to others in the organization. And yet, he is treated on the same level as a partner rather than a subordinate – he has a secretary and is in charge in a number of ways, but he never technically reaches the top of the mountain. This seems to be one of the risks of being a renegade. It might mean that you are never officially appointed to the very highest roles because people fear what you might do once you get there. 

78. Michael Corleone, (The Godfather, 1972)

“Don’t ask me about my Business”

It was perhaps tempting to place Michael Corleone (played by Al Pacino) in the psychopathic managers category. After all, he is a cold blooded murderer who runs a crime family and even ordered the ‘removal’ of his own brother from their organization. However, Michael has a more complex tale than simply using pure brute force and violence to get his way  – the application of cunning, patience and timing goes a long way towards creating renegade manager of this sort. Wilder, randomly violent characters like his brother Sonny rarely raise to the position of crime boss, they are eliminated way before they reach those kinds of heights. To understand Michael it is important to go back to the beginning: his father Vito Corleone (played by Marlon Brando), the boss of the family business. Vito saw great promise in his son, Michael but Michael himself had no desire to go in to the family business. Instead, he enlisted in the marines and rose to the position of captain. Eventually, after years of resisting and watching his father suffer repeated assassination attempts Michael decides to cross the line and murder the people responsible, one of whom is a police officer. It was generally agreed that police were “off-limits” for mafia hits, but Michael (being the renegade that he is) decided that this rule was obsolete – they were threatening his family and they had to die. He shoots the two dead in a restaurant in a now famous and incredibly tense scene and in that moment becomes the man his father saw in him – the future boss of the Corleone crime family. 

The Godfather is essentially a character study about how a young man develops and changes over time – honing his skills and inner qualities – to become the head of a ruthless organization. As Al Pacino suggested about playing Michael, it “was and still is the most difficult role I’ve played. I didn’t see him as a gangster; I felt his power was his enigmatic quality.” The fact that he is a renegade and knows when to break the rules but also when to keep to them and bide his time, is exactly why he is so suited to become the Godfather. We, the audience, experience this unknowable quality within Michael on numerous occasions in the film, not least in the restaurant scene mentioned above where we simply do not know what he is going to do. Some articles now point towards the leadership lessons found within The Godfather, which suggests of Michael: “While he is not without flaw, he represents a leader that can see through a fire. He sees what is needed tactically without being myopic while fulfilling the strategic vision of the family but not getting lost in the big picture. When everyone is struck by shock and calamity, Michael is able to stay calm and see through the fire and guide everyone with a solution. Any company and team with a Michael is sure to succeed.” This is reflected in Michael’s quick actions once his father dies. He takes the reins as Don and moves quickly and ruthlessly to eliminate his family’s enemies. He kills the heads of several families he knows are plotting to oust him and ensures that through being one step ahead of his rivals he will achieve success for the family business he has inherited. This is ultimately the power of the renegade boss – they see what others do not see and know exactly what to do and when to do take decisive action. It is possibly why they are such attractive characters in popular culture. Most of us are either too impulsive or too indecisive and fail for those reasons – these managerial characters have impeccable timing. 

79. Rick Blaine (Casablanca, 1941) 

Customer: Um, waiter? Will you ask Rick if he will have a drink with us? Carl Headwaiter: Madame he never drinks with customers. Never. I have never seen it. Customer: What makes saloon keepers so snobbish? 

German Banker: Perhaps if you tell him I run the second largest banking house in Amsterdam? 

Carl Headwaiter: Second largest? It wouldn’t impress Rick. The leading banker in Amsterdam is the pastry chef in our kitchen.

We meet Rick Blaine (played by Humphry Bogart) as the cynical owner/boss of Café American, a drinking and gambling hangout located in Casablanca, Morocco. World War Two is raging in Europe (as it was in the real world at the time) and German officers, Vichy police and people fleeing the continent flow through the bar, run by an ice-cold Blaine who states quite clearly “I stick my neck out for *nobody*”. He is the predictable, capitalist manager. In it for the money and on the side of himself, and himself alone. Or so it seems at first. We slowly learn through his Vichy police patron, Captain Louis Renault, that Rick has a more complicated history, having fought against the Nazis in both Spain and Ethiopia. We also learn from flashbacks that the reasons for Rick’s ice-cold persona is a broken-heart. Many years ago in Paris we see him as Richard, an idealistic man in love with Ilsa Lund, a young Swedish woman  (played by Ingrid Bergman). Fleeing Paris as the Nazi’s invade he is supposed to leave with Ilsa but she stands him up breaking his heart. The sadness and detachment he now carries as he runs his bar and moodily orders his employees around stems from this terrible moment from his past. 

The film takes a massive turn when in to Café American walks Ilsa, with her new lover, a spy called Laszlo. She begs Rick to help her and Laszlo secure letters of transit so that they can flee the impending Nazis and get to the safety of Switzerland to continue his work. It is at this point (after some initial jealous resistance) that Blaine reveals himself to be willing to break all the rules to help the couple escape. Whilst we see Ilsa and Rick pine for each other (with Bogart standing on a box apparently to remain taller than Bergman during scenes!), he sets this aside ultimately for the greater good. Casablanca is one of the most quotable films in film history and ends with one of the best (albeit one that was dubbed in after the films ending in post-production because the producers felt the original final line was too bleak). As Rick watches the aeroplane take Ilsa and Laszlo away to safety he says to Vichy friend (who had also assisted with their escape) “Louis, I think this could be the start of a beautiful friendship.” While Rick began the film as a cynical, apolitical manager of a café, he had revealed himself to be somebody entirely different (as had Louis in letting them go). 

It is an important reminder that managerial appearances can be deceptive and that we only find out what someone is truly like when their back is to the wall and they asked to choose between doing nothing (and aiding evil) and doing something (and keeping some good in the world). Warner Brothers who produced the film purposefully infused an anti-isolationist message within the film to try and convince America to enter the war in 1941 and stop standing by coldly as good people were killed. The Café American, in this sense, is a microcosm for the world; filled with people of all nations and races and Blaine is essentially America – a cold, detached manager, who has the potential to do good but is traumatised by his past. Blaine is a lesson that nations, people and, indeed, bosses can look beyond their own selfish, personal needs, rebel against evil and do good in the world. 

80. Gregory House (House M.D., 2004)  

“It is in the nature of medicine, that you are gonna screw up. You are gonna kill someone. If you can’t handle that reality, pick another profession or finish medical school and teach.”

A typical day in the working life of Gregory House MD goes as follows: a patient presents themselves to his team of junior doctors as having a range of symptoms that make no sense to normal doctors. They are stumped and have no idea what is wrong with them. House is called in as a maverick doctor who slowly puts together the evidence to cure the patient from what usually turns out to be an obscure or difficult to identify ailment. Indeed, it is widely accepted that House was based on Sherlock Holmes with Hugh Laurie (who plays House) admitting in an interview that the “cold, calculating, mechanical” nature of the character’s thought process mixed with his immense passion for science and music was consciously based on the Arthur Conan Doyle’s detective. This enables House to make connections between logical facts that others simply are no capable of. In one episode a man is admitted to his teams care with a swollen tongue sustained whilst engaged in sexual relations with his wife. House becomes convinced that the wife is poisoning her husband but has no way of proving it until he eventually realises through testing that she is using an extremely rare form of gold poisoning that was especially difficult to detect.  One blog, Polite Dissent, goes in to meticulous detail about each episode and from an actual doctor’s point of view. Some episodes are deemed incredibly realistic and others in the realm of fantasy and not what would actually be diagnosed at all. 

Laurie suggested one of the things that drew him to the character of Gregory House was that “he didn’t try to be liked”. House is an incredibly difficult boss and many of his younger recruits (who he often refers to merely by numbers or nicknames) suffer at his hand but remain in awe of his incredible talents. One of the strange things about maverick or renegade managers is that they tend to be able to get away with being absolutely awful (and borderline abusive) towards those serving underneath them. This underlines a cultural acceptance that if somebody is considered brilliant or exceptional in the work-place, their actions and behaviour are also judged in an exceptional light as well, enabling them to get away with things that other people might not. House for example (like Holmes) has a drug addiction that he uses to mask physical and mental pain he experiences through his role and a leg injury he receives. Whilst he does get in to trouble for using and abusing the opioid Vicodin he is never struck off entirely which one might expect would happen with any “normal” doctor. One of the main reasons doctors like this (in fiction at least) get away with these things is because they can do what others cannot and can teach those lesser mortals working underneath them things that they otherwise would never know. Aspects of the show have even been influential in real-life. In 2012 German doctors admitted to diagnosing a patient with Cobalt poisoning based in part upon remembering the symptoms from an episode of House. In the episode a patient had developed mysterious symptoms including a fever and heart troubles and had eventually (thanks to the genius of house) been deduced to have had fragments of her cobalt hip replacement seep in to her blood stream. This reflects the sheer influence and genius of the renegade boss that goes to make them so exceptional in organizational situations – sometimes for good and sometimes with much darker consequences. 

81. Steve Jobs (Steve Jobs, 2015)   

Steve Wozniak: You can’t write code… you’re not an engineer… you’re not a designer… you can’t put a hammer to a nail. I built the circuit board. The graphical interface was stolen from Xerox Parc. Jeff Raskin was the leader of the Mac team before you threw him off his own project! Someone else designed the box! So how come ten times in a day, I read Steve Jobs is a genius? What do you do?

Steve Jobs: I play the orchestra, and you’re a good musician. You sit right there and you’re the best in your row.”

Apple has long positioned itself as a renegade organization. Their now infamous “think different” ad campaign in which they flash pictures of Bob Dylan, Einstein, Martin Luther King etc which is narrated by Chief Executive and co-founder Steve Jobs goes as follows: “Here’s to the crazy ones, the misfits, the rebels…the ones that see things differently. They aren’t fond of rules and they have no respect for the status quo…they change things, they push the human race forward.” When Steve Jobs first heard the pitch he thought for a few moments that it would be too self-indulgent and that the media might further think he and Apple were on a massive ego trip. He quickly lost these reservations, preferring to think instead (correctly some might say) that the ad was accurate – they were pushing things forward and thinking differently compared to their rivals. One of the most peculiar media phenomena of our time is the emergence of the CEO biopic which buys in to this romanisation of the managerial classes as an elite that can indeed change the world if they are brave enough and take enough risks. Hollywood stars (usually infinitely more attractive and charismatic than the real life manager) play an exaggerated version of the individual to mythologise them and their role in the organization in an effort to create a more entertaining and watchable film.  

The 2015 film Steve Jobs (in which Jobs is played by Michael Fassbinder) is a great example of this genre of film. A decent and entertaining film but through which very little actually happened as was portrayed. One fact-checking article, which compares the movie to what actually happened according to Apple employees, states more or less every scene within the film was a fabrication. From confrontations Jobs had to reconciliations and touching moments with his daughter and all manner of other instances which one might hope have at least some grounding in reality. And yet the writer of the film, Aaron Sorkin, explains that his film is purposefully not a birth to death biopic – it is a “painting not a photograph”. The aim is to capture the man not through exact replication of events but through broad brushes that embody who he was and what he stood for. In an interview Sorkin explains about working on his first film and what this taught him about translating truth in to film: “[I was working on] Charlie Wilson’s War, with Mike Nichols, [it] was the first nonfiction that I wrote, and there was this thing that Mike would repeat to me: “Art isn’t about what happened.” That sunk in.”

The film itself is presented in three parts around three Apple product launches and the professional and managerial difficulties in doing so. The  sad truth is, perhaps, that managers and management are 99 percent of the time incredibly boring. So portraying these product releases as they happened without dramatization and fabrication in a Hollywood film is not going to get you the great reviews and accolades the film eventually received. 

In terms of who Jobs actually was, he could by all accounts be harsh and abrasive. Brutal even. In one real-life story Jobs learned that a Google employee had sent a jobs pitch to an Apple employee about upcoming openings at the search engine company. At the time Apple had an informal (and technically illegal) agreement with Google not to poach each other’s employees to keep wages down. Jobs allegedly emailed Google Chairman Eric Schmidt and within the hour the Google employee had been fired. The response of Jobs via email when told of the employee’s dismissal at his hands? A smiley face.  Many viewers (especially those who knew Jobs) have reacted angrily or at least disappointed at the misrepresentation of Steve Jobs within the film. To some it created an entirely new character that Sorkin himself found more interesting and overlooked the emotional components of the man. One New York Times column even likened Sorkin’s portrayal to a “con“. In this article Joe Norcera states: “the film simply doesn’t understand who he was and why he was successful. For instance, one character mentions Jobs’s ability to create a “reality distortion field.” But we never see the charismatic man who could convince people that the sky was green instead of blue.” Despite this, the film does still to some extent tackle the extent to which Jobs was a maverick and it was difficult to define just what his magic touch was. At one point in the film, Steve Wozniak asks Jobs what is it that you do? As alluded to in the quote at the beginning of the entry, Jobs saw himself as the conductor of the orchestra. He could see the big picture whilst other geniuses focussed on the details. Whilst, again, this conversation did not happen in real life, Sorkin and the director Danny Boyle bought in to words that they felt captured the spirit of this renegade boss and the je ne sais quoi that they have about them. 

“We’re all partly responsible for that,” said Boyle in a Guardian interview  “We all bought into it, especially in America. He’s a businessman really, but in America it’s part of the myth of the frontier: the pioneer. One man forging ahead, breaking through any barrier.” 

82. Don Draper (Mad Men, 2015)  

“What you call love was invented by guys like me… to sell Nylons.”

Don Draper (played by John Hamm) is advertising executive at Sterling Cooper advertising agency in 1950s America. It is a time when the power of advertising, to sell tobacco, perfume, toys, cars and any number of products is truly being recognised on a large scale for the first time. Madison Avenue is born and advertising is considered big business. Donald Draper is the shining star of the organization. Whereas one man might think of a run-of-the-mill advertising campaign, Don has the capacity (the intelligence, the looks, the style and the charm) to walk in to any room of business executives and tell them how their product should be sold for maximum affect and profit. In one infamous board room scene Draper is pitching to Kodak about their product. He tells them it’s not just a camera, it’s a time machine and he evokes the notion of a carousel to sell the advert to an open mouthed clearly very moved bunch of Kodak executives. This is the power of advertising on these middle aged men, but also a clear sign of the hypnotic effect of advertising and what is increasingly going to impact and influence the rest of the world, particularly through the advent of TV. And yet, Draper himself is hiding a secret: “Don Draper” himself (the king of advertising) is an advert used to sell his talents most effectively. We learn over time that he wasn’t born Don Draper, he was born Dick Whitman and was born incredibly poor during the 1930s recession period in the Midwest countryside. He was neglected and abused as a child, growing up in a brothel. The polished, final version of a man we see now, leading successfully is a glossy cover for what is going on beneath the surface.  

Don Draper is one of the most complex and fascinating characters to come out of the past thirty years of television. There are a number of candidates or bosses on whom Don Draper was based, including Draper Daniels, the man who created the influential Marlboro Man campaign. The Draper we encounter is equally daring and captivating in the adverts he creates and promiscuous in his relations with women. He is a deeply flawed individual who (at times) does terrible, amoral things but who has  enough goodness and kindness in them to persuade an audience that they can be redeemed. He attempts to builds a sense of status and importance through his job so as not to be so unfulfilled and miserable. In one scene, Don Draper advises one of his workers ‘you’re happy because you’re successful – for now. But what is happiness? It’s a moment before you need more happiness. I won’t settle for 50 percent of anything. I want 100 percent.’ The tragedy of Draper as a manager and as a person is watching him pursue the impossible (the 100 percent), of something he can never achieve, and destroying everything and everyone he has in the process. The ultimate irony of the show is in the very last scene we are led to believe that Draper (suffering from a creative block) might have finally found spiritual peace, meditating with hippies on a hilltop colony far away from his management desk. However, the show ends with a wry smile from our meditating protagonist and jumps to the now-iconic Coca-Cola ad ‘I’d like to teach the world to sing’ complete with dancing hippies on a hilltop colony, suggesting that he has used this experience to create one of the most successful ad campaigns of all-time. Draper as a manager will never find peace; he will always be innovating and striving, searching for the 100 percent. 

The danger of this morally murkier vision of the manager in fiction, however is that it slips into nihilism. Characters like Tony Soprano and Don Draper are now counter culture heroic figures who might in any sensible world act as warnings about male unhappiness but instead are regularly celebrated on websites glorifying their best quotes without any sense of irony. In one interview, John Hamm talks about Draper as having manufactured confidence in a work setting and being very different from his alter-ego (Dick) that we see occasionally in the show. “Don had a different way of carrying himself,” Hamm said. “There was this performative aspect to Don, when he was in the office especially… that was very much a conscious decision.” It seems that one of the central messages of the show is that whilst you can be a brilliant, charismatic, renegade manager on the surface – admired and respected by all – much of what it takes to achieve this has to be a performance. In another interview with Hamm when asked if he takes any of his own performance of Draper home with him in to his real life. His response is telling: “Don Draper is a pretty dismal, despicable guy, so why I would want to take him home with me I don’t know… It’s a strange thing. People tell me they look up to Don, like they look up to Tony Soprano or Walter White [in Breaking Bad]. People have these weird fascinations with people who in reality you would not want to be for a second. There seems to be that vicarious thrill. Maybe it is the fact of doing everything wrong and getting away with it.” The same seems to be the case for wanting to be the renegade manager, who breaks rules and cuts corners without any of the consequences – culturally, to me at least, this has shaped what we consider a successful boss to be with quite worrying ethical consequences. 

Identity Nine: The Predatory Boss

This identity relates entirely to sexual predation, and can range from unwanted sleazy jokes or innuendos right up to sexual assault or rape. An identity of this kind is undeniably built around power and control and asserting dominance through a capacity to make others do what they otherwise wouldn’t. While in the past many women suffered sexual harassment in the workplace, it hadn’t even been given the name as such and women tended to keep quiet about it, with the express aim of keeping their jobs and hoping that the unwanted attention simply went away. Meanwhile, within fiction, sexual harassment in the workplace was largely considered a laughing matter (the “Carry on..” films and Benny Hill spring to mind). In recent years however the #metoo movement has helped to shine a light on the dark underbelly of predatory behaviour in the workplace. The case of Harvey Weinstein, for instance, captures a manager (film executive at Miramax) forging an identity around sexually predatory behaviour. Nowhere explores this better than Jodi Kantor and Megan Twohey’s, She Said, a 2019 Pulitizer winning book detailing the creation, continuance and eventual downfall of Weinstein’s managerial identity and with this his career. How he, as “a powerful boss…used the pretext of business meetings to try to pressure women into sexual interactions, and no one did anything about it” (33). He assaulted and raped numerous women in the TV and film industry through manipulation, lies and at times sheer brute force. 

And yet within the management discipline itself, there is very little written about these types of bosses – how they become these kinds of predators and how they sustain their positions thereafter. Let alone how these kinds of predatory identities can be challenged early on and stopped. There are many examples of these predatory characters in TV and film – most not nearly as bad as Weinstein, but certainly part of a cultural view of the boss and the power that they have to control subordinates in ways that they certainly should not. Here are eight powerful examples of this, some humorous (attempting to make fools out of the predators themselves), some deadly serious and others in the grey areas inherent to these areas of discussion: 

83. Jeff D. Sheldrake (The Apartment, 1960) 

C.C. Baxter: You’re not going to bring anybody to my apartment. 

J.D Sheldrake: I’m not just bringing anybody; I’m bringing Miss Kubelik. 

C.C. Baxter: Especially not Miss Kubelik. 

J.D Sheldrake: How’s that again? 

C.C. Baxter: [firmly] No key. 

J.D Sheldrake: Baxter, I picked you for my team because I thought you were a very bright young man. Do you realize what you’re doing? Not to me, but to yourself? Normally, it takes years to work your way up to the twenty-seventh floor. But it only takes thirty seconds to be out on the street again. You dig?

One of the central characteristics of the predatory boss is an ability to abuse positions of power and knowing exactly how (and when) to do so in order to get their own way. Billy Wilder’s 1960 romantic comedy The Apartment is an acerbic take on how businessmen in offices use and abuse women for their own gratification and further their own interests. Indeed, whilst Wilder’s film is a comedy, it was meant as a dark insight in to office politics and the implications of this kind of behaviour. In many respects it speaks to the issues we find addressed within #metoo a full fifty years before the emergence of the movement – a film, as many of Wilder’s films were, way ahead of its time. The Apartment follows an insurance company employee C.C Baxter (played by Jack Lemmon) as he tries to climb the greasy pole of the insurance industry, using his well-placed apartment to loan out to executives needing a place to take their mistresses. One day however, the Director of Personnel, Jeff D. Sheldrake (played by Fred MacMurray), invites Baxter to his office, seemingly to reprimand him for bringing the company into disrepute with his extracurricula activities. But after their meeting is interrupted by a phone call from Sheldrake’s wife, in which he tells her that he will be ‘entertaining’ the ‘branch manager from Kansas City’ that evening, he ends up persuading Baxter to give him exclusive access to the apartment. He promises Baxter that in exchange he will be considered ‘executive material’ in the next reorganization. He keeps his promise: Baxter gets a series of promotions in the course of the film – he ends up on the Executive floor – simply because he was so cooperative.

The person Sheldrake was ‘entertaining’ that evening was one of the company’s elevator operators, Fran Kubelik (played by Shirley MacLaine), a young woman Baxter would very much like to date himself. Sheldrake and Kubelik conduct their affair in Baxter’s apartment – albeit Kubelik is unaware of whose apartment they use. In any case, she is deeply ambivalent about the affair – Sheldrake keeps saying he’ll leave his wife, but keeps failing to do so. Kubelik’s suspicions are confirmed at a riotous office Christmas party where Sheldrake’s secretary (somewhat the worse for alcohol) confides to her that Kubelik is just the latest in a long string of Sheldrake’s mistresses from the company. Clearly deeply upset, Kubelik confronts Sheldrake in Baxter’s apartment. But Sheldrake regards her distress merely as an inconvenience – he quickly leaves to join his wife and family (it was Christmas Eve). He disposes of Kubelik by stuffing a hundred dollars in her handbag as a Christmas present – an act which makes her feel like a sex worker. As she washes in the bathroom after Sheldrake has gone, she spots a vial of Baxter’s sleeping pills in the cabinet and attempts suicide. Baxter gets home to discover her lying unconscious in his bed. Doubtless she would have died if his neighbor had not been a doctor willing to pump her stomach.

Although The Apartment was released almost 60 years before the #MeToo movement, the character of Sheldrake invites a more or less direct comparison with Harvey Weinstein. Sheldrake is clearly not meant to be a sympathetic character – he appears to us as unambiguously loathsome, vulgar, cynical and cruelly womanizing – not to mention close to repellent physically. (Not just to us: MacMurray reported that after the release of the film it was not unusual for women to accost him on the street and tell him he was disgusting.) Furthermore, he operates near the top of a corporate environment that encourages people to mimic him. In a particularly gruesome scene, the group of middle managers who had originally used his apartment for their early evening trysts call in at the apartment to ask Baxter to let them start using it again – just at the time when Kubelik is asleep in Baxter’s bed, recovering from her overdose. Catching a glimpse of her in his bed, they delight in telling Baxter that he’s really ‘hit the jackpot this time’ and that they can now understand why he has stopped them using his apartment. But their misogynist delight is nothing to do with what, in their terms, is Baxter’s good fortune. Rather, it was the potential ammunition their discovery gave them to use against Baxter. Indeed, the tone of the film, which presents crude misogyny and gross sexual exploitation being rewarded by promotions is pervaded with a darkness relieved only by moments of uncomfortable humor, and possibly by Baxter’s feckless innocence – in an otherwise degenerating world.

84. Franklin Hart Jnr (9 to 5, 1980)  

“You tangle with me, and I hope you’re prepared to play dirty and rough. I’ll be damned if I let myself be stopped by three dim-witted broads!”

In Patricia Resnick’s feminist revenge comedy 9 to 5 Dora-Lee Rhodes (played by Dolly Parton) dreams and schemes with her colleagues about how to get revenge on their “sexist, egotistical, lying, hypocritical bigot” of a manager. When he isn’t trying to sleep with the women in the Consolidated Companies office department he is saying some pretty awful things and being the kind of misogynistic boss that was common-place in offices in the 1970s and 80. In one hilarious scene he three women fantasise with a joint about what they would do to their predatory boss if they had the power for a day. Fortunately for them that day has arrived as the three women feed Franklin rat poison and lock him up out of sight determined to get their revenge. Originally Resnick had also planned in her script for the women to actually kill their boss but this was deemed as too dark and re-written. Instead, and perhaps more radically, the women fake their bosses signature to bring about a complete overhaul of the office including installing a creche, re-hiring unfairly dismissed female workers and implementing equal pay. Fascinatingly, the idea for Dora-Lee (Parton’s character) came when the writer of the film (Patricia Resnick) visited Fox Studios’ insurance company. In an interview she revealed: 

“This is actually the genesis of Doralee, the Dolly Parton character. There was the head guy’s secretary. I had spent some time with some of the other secretaries first before talking to her, and nobody liked her. Everybody had a bunch of awful things to say about her, and they said she got to be his secretary because she was sleeping with him, and on and on. I finally went out to lunch with her one day, and she had a couple of martinis and her tongue got pretty loose and she started telling me about her life, and she started crying. She was a really nice woman, she was living with her mom and taking care of her, and she knew everybody thought she was sleeping with the boss, and she said she wasn’t. That gave me the idea for that character.”

In response to people who look back on 9 to 5 with snooty derision, seeing it as caricatured, a 2018 article on the British Film Institute website declared that “yes, 9 to 5 really is a feminist movie.” It is hard to argue against this assertion, as it broke new ground in Hollywood film making, paving the way for films who later went on to take these issues more seriously (see 2019’s The Assistant as a fantastic example of this). Interestingly, it often takes comedy films (like The Apartment [1960] before it) to break down walls and bring issues like predatory bosses to the fore. There is no better example of this than the out-takes from the film which are hilarious even to this day, reflecting the difficulties in portraying these office scenes and rather intense boss-worker interactions. 

85. Dr Julia Harris (Horrible Bosses, 2011)  

Dr Julia Harris: “Look, Dale, you know… I know I like to fool around at work, right? And I might even, you know, I might even cross the line a bit. But the last thing I wanna do is make you uncomfortable. I mean, it’s just not professional, you know? And I pride myself on being a professional. So from now on, what I would like you to do is just tell me, you know… when and if, uh, I cross the line. Okay?” 

Dale Arbus: “Okay. Now” 

Dr Julia Harris: “What?” 

Dale Arbus: Well, now, you’re kinda crossing a line… because you’re naked”.

Dr Julia Harris: “Uh… I’m not naked, Dale. Can you *see* my pussy”

Conventionally, we are used to seeing men as predatory bosses in TV and film. That is, of course, reflective of reality in an organizational life. The vast majority of sexual harassment in the workplace originates from men and is against women. However, an increasing number of sexual harassment complaints are now submitted by men, with a 2015 reportsuggesting around 17% of complaints submitted by men to the US-based Equal Opportunities Employment Commission. Obviously some of these will include male on male sexual harassment (there is no breakdown on this aspect) but instances of unwelcome sexual advances by women on men as well as retaliation for turning them down are now regularly reported. In 2011’s Horrible Bosses we meet a boss exactly of this kind, in the guise of Dr Julia Harris (played by Jennifer Aniston). As stated in previous entries (28 and 39!), Horrible Bosses is a film about three employees each who have an awful boss who they want to get rid of, by any means necessary. Harris is the manager of a dental surgery who is for all intents and purposes a nymphomaniac, Harris regularly strips naked (or semi-naked) in her office in an attempt to seduce Dale Arbus (her dental assistant) but is regularly rebuffed due to the fact he has a fiancé and is a loyal guy. Not to be deterred she goes to great lengths in an effort to he takes pictures of Dale whilst he is passed out naked, and threatens to release them to his fiancé unless he sleeps with her. This leads Dale to try and get rid of boss by hiring a contract killer that will remove her from his life once and for all. 

Horrible Bosses, let us remind ourselves, is a comedy film. Incidentally, Horrible Bosses 2 also stars Dr Julia Harris and it was revealed in one article that they filmed a scene (which was left out of the cinematic release) in which she sleeps with Dale whilst he is in a coma. Aniston herself relished the role as like many of her Friends co-stars she has long been trying to move on from being remembered, in her case, as Rachel from Friends, a nice, fun but ultimately quite dull character. For Aniston, playing Harris was “fun, uninhibited and…full of freedom” because it was so different to the characters she has been used to playing. Similarly, these characters are not ones we are used to seeing on screen. And whilst the film has come under fire, there is a sense that the makers were purposefully playing with the idea that we aren’t used to seeing women being so hyper-aggressive on screen, and so were encouraged to push this depiction of a nymphomaniac boss to its limits. However, one of the most unintentionally disturbing things Aniston has had to say about the film is citing her co-star Kevin Spacey as being so influential for her role in the film. Whilst Aniston presumably meant that Spacey was an acting inspiration on set, in 2018 Spacey was himself charged for sexual assault with an aspiring actor and has had to answer a string of allegations against him. Perhaps Aniston knew more than she was letting on, or perhaps it was a strange coincidence. In any case, it demonstrates how ingrained sexual predation is within Hollywood both on and off screen. One wonders how much films like Horrible Bosses undermine such behaviour by lampooning it or conversely normalize it by making it appear harmless and fun. 

86. E. Edward Grey (Secretary, 2002) 

“When people come into this office, you are a visual representation of my business. And the way you dress is disgusting” 

Secretary (2002) is a dark comedy about a young woman called Lee Holloway (played by Maggie Gyllenhaal), who following her release from a mental institution finds a job at a legal office. She is installed as a secretary to Edward Grey (played by James Spader), an old-fashioned disciplinarian who gradually realises he is sexually aroused by telling his submissive secretary exactly what to do in her role. In the intriguing opening scene of the film, we find her happily conducting her duties as a secretary whilst handcuffed to a rod that rests on both of her shoulders. Later we see her crawling with a saddle on her back in the office with a letter (and later a carrot!) in her mouth. Most importantly, this relationship is not only entirely consensual, but very much a two-way street – Grey is every bit as much scared of his unfolding behaviour as Lee is comforted by her own submission to it. Gradually we witness the development of a relationship built around control and submission that doesn’t appear to be exploitative at all, but of a “predator” and “prey” knowingly engaging in a dance that they are both fully aware of and perhaps had always been looking for in another person. The fact that it is between a boss and a secretary is a darkly humorous piece of social commentary that the film lightly makes throughout. 

Bizarrely, and I assume entirely unintentionally, Edward shares his final name with another Mr (Christian) Grey which would later capture the imagination of middle class housewives in E.L James’s 50 Shades of Grey. Some readers/viewersare less certain of how “accidental” the overlaps are between these pieces of fiction, but I suspect the name Grey might be an obvious misnomer to fall back upon for any writer in this genre. Edward Grey is certainly not a billionaire (he has a modest law firm) nor is he as sure of himself as Christian about who he is and what he is becoming. In one interview(conducted at the time of filming the movie) a clearly immersed Spader suggests Grey is “lost” and unsure what to make of his perverse thoughts. He suggests that he has an “enormous…[purposeful pause] appetite and ravenous hunger…with which he is constantly in conflict with…His desires are assimilated in every aspect of his life…constantly reminding him of his desires, wherever he looks, wherever he turns.” Spader has made a career out of playing bizarre and perverse characters (see David Cronenberg’s 1996 film Crash for a film that makes Secretary look extremely tame in comparison), and he embodies Grey so precisely, capturing the sheer excitement (and terror) of realising not only who he is but having an employee who is ready and willing to go along with him on this journey of self-discovery rather than quit the job after a few days. 

In the #MeToo era, the film could have been in danger of being unfairly accused of misogyny and lazily interpreted as a film about male domination and female subjugation in the workplace. The film almost playfully invites you to jump to this conclusion. Too often the secretary in fiction has been portrayed as weak, meek and powerless. During the 1940s the Underwood Corporation (in the US) even financed short films for aspiring secretaries to educate them about the duties they were expected to undertake and master. Whilst somewhat humorous to watch today, the films clearly infantilise the secretary (teaching her how to do fairly menial tasks) and setting her up in a servile role to her master (the boss) in a way that was reproduced by countless secretaries across the country. In other early films such as Wife vs Secretary  (1936) (starring Clark Gable and Jean Harlow) themes around flirtation and infidelity between bosses and their female assistants were also playfully explored. These fictional portrayals reflected a sexualisation of the secretary in popular culture which is continued in films noted in the list above including The Apartment (1960) and Working Girl(1988) and TV shows such as The Rise and Fall of Reginald Perrin (1976)  and, more recently, Mad Men (2007). These representations have in no small part perpetuated cultural attitudes about secretaries that positions them as both predators and/or prey. The idea of the “meek secretary” ready to be taught contrasted with the “sexy bespectacled secretary” and the innocent but worn down boss being seduced by her. 

However, the film Secretary somehow manages not to fall in to a clichéd or stereotypical trap of this kind. And neither do its characters. It contains predatory behaviour but it is the one example in this group which is consensual. Moreover, it is desired predation from two characters each for one another in very different ways and for polar opposite reasons. Lee and Edward are co-dependent. Each knows who they want and who they need to be happy and whilst it is not the usual simplistic answer we find in films it is undeniably the right one in the circumstances. The film has in fact been celebratedas an empowering look at a different kind of relationship. Erin Cressida, co-writer of Secretary, summarised this fantastically well in one interview:

“‘Secretary’ doesn’t politicize the sexuality or the relationship. It doesn’t insist on taking sides. Also, it doesn’t seek to solve problems. The secretary does not seek to get over her masochism as if it were a deviant problem. She actually embraces it. It also turns clichés on their heads. Instead of her running to arrest him and screaming equal rights, she falls in love with him. And he in turn gets afraid. She owns her submissive quality.”.

She goes on: 

“In the ‘80s, it seemed there was a lot of anti-male sentiment. To be a real feminist, it was less OK to be rampantly heterosexual. That was my experience. So now my reaction was to insist you could be a feminist and you could be a three-dimensional woman and still love men. I was brought up as a feminist. Maybe the movie represents a wave of feminism that hasn’t been named.”

Secretary is a ground breaking film in this sense. In its depiction of a bizarre but beautiful workplace relationship is wrapped up with consensual predation in a way that no other film I can think of achieves. It stands out in this section for depicting a male predatory boss who we aren’t reviled by but are instead intrigued and even (potentially!) excited by. 

87. Meredith Johnson (Disclosure, 1994)  

“I am a sexually aggressive woman. I like it. Tom knew it, and you can’t handle it. It is the same damn thing since the beginning of time. Veil it, hide it, lock it up and throw away the key. We expect a woman to do a man’s job, make a man’s money, and then walk around with a parasol and lie down for a man to fuck her like it was still a hundred years ago? Well, no thank you!”

The 1990s was a strange time for female empowerment in Hollywood film. Time and time again hypersexualised women (“femme fatales”) dominated men, appearing on the surface at least to be powerful, with the somewhat predictable consequence of becoming objectified sex symbols for that very reason. They were empowered, but dangerous and almost portrayed as precautionary tales – modern day Jezebels. From Sharon Stone uncrossing her legs in the interview room of a police department in Basic Instinct (1992) to Madonna seducing and killing men in Body of Evidence (1992), Hollywood seemed finally to want to depict powerful women, but in a way that left the viewer asking: Is this female empowerment in the guise of sexual predation? Or sexual predation in the guise of female empowerment? Or something entirely different? Maybe both working in tandem. The 1994 film Disclosure covered similar (albeit slightly less deadly) ground, but this time exploring the consequences of a femme fatale trying to “kill” the career of a man in a large computer company. The story goes as follows. Digicom are embarking on a merger and while Tom Sanders (played by Michael Douglas) expects a promotion to CEO, his colleague (and former girlfriend) Meredith Johnson (played by Demi Moore) gets the nod instead. She invites Tom to her new office and forces herself on him. When Tom (now happily married) rejects her she is livid and the very next day accuses him of sexual harassment, leading to a company investigation and an attempted cover-up, encouraging him to leave. 

In one interview Demi Moore described Meredith as “extremely ambitious, smart, very clever and [a woman who] has a complete sense of herself and the power she contains.” Moore suggests it was interesting “step[ping] in to the shoes of someone who enjoys manipulating and controlling people without realising that there is anything wrong with it – with no remorse.” She admits to finding it emotionally “frightening” playing such a woman and that at times she tried to (unsuccessfully) convince the director to “row back” and sensor some of what Meredith was saying and doing. None of us (including Moore herself) were used to seeing such powerful, sexually aggressive women in Hollywood films, and the film did make good at the box office. One might cynically wonder whether these femme fatale films (mostly written and directed by men) are merely part of a wider exercise in fantasy inaction through the sexiest and most attractive women in Hollywood being imagined as, for instance, sexually aggressive bosses who were ready to take charge. In the film, Tom eventually proves that Meredith is not as innocent as she is making herself out to be and he returns to his Head of Manufacturing position. If the makers of the film were seeking to invert roles of men and women in traditional cases of sexual harassment in the workplace, then a more logical route would be to have Tom resign, ashamed and embarrassed by an inept corporate and legal system, and grudgingly signing a non-disclosure agreement so he could continue to pay his rent. But this is Hollywood, and a happier (arguably less realistic or interesting!) ending was apparently on the cards for Tom and Meredith. 

88. Margaret Tate (The Proposal, 2009)  

Margaret Tate: “What am I allergic to?” 

Andrew Paxton: “Pine nuts, and the full spectrum of human emotion.”

The inclusion of Margaret Tate (played by Sandra Bullock) in The Proposal might be considered somewhat harsh on the character. However, when we break down exactly what happens in this movie it becomes a bit more clear why she is a predatory manager. Margaret is executive editor-in-chief of a New York book publishing company. She is a mean boss, working her employees to the bone and is generally feared within her department. She is particularly mean to her personal assistant, Andrew Paxton (played by Ryan Reynolds). Margaret learns that she has invalidated the terms of her visa and so is going to be deported out of the USA losing her job unless she can convince an American citizen to marry her. She proceeds to coerce Andrew to marry her so that she can achieve this goal. Despite the film being dressed up as a romantic comedy and (of course) it ending with Paxton falling in love with Tate, the basic message of the film has long struck me as rather odd. It is not always sensible to say “what if the roles were reversed” but in this case, I think it reveals the rather disturbing power dynamic at work in their relationship and normalizes bosses asking their employees to go to wildly inappropriate lengths to keep them happy. In my eyes, this film joins the list of romantic comedies that have aged incredibly badly over time. This includes films like Never Been Kissed (in which an adult teacher develops feelings for what he considers to be a teenage school child), and The Breakfast Club, a film that has aged so badly that lead actress Molly Ringwald wrote a long (extremely good!) New Yorker essay about the problematic misogyny found within it. Ultimately, whilst it isn’t always obvious at the time the way that films age and change in the viewers minds is a fascinating aspect of the evolving nature of (amongst other things) managerial identity. 

89. Roger Ailes (Bombshell, 2019) 

Roger Ailes: Great, the future of Fox News is now a goddamn feminist.
Megyn Kelly: No, I’m not a feminist. I’m a lawyer.

One of the most difficult things about predatory bosses is actually getting them to admit their wrong-doing. As we have seen with the Harvey Weinstein case, in the movie producer’s eyes it was everybody’s fault but his own. The convenient myth of the “crazy bitch” in organizational life, making up stories to ruin men’s lives and stir up trouble has existed for as long as women have been in the workplace. Bombshell is a film based on a true story in 2016 that explores the efforts of three women in particular, and their attempts to expose CEO Roger Ailes’ sexual harassment in the broadcast news corporation.  Ailes (played by an unrecognisable John Lithgow in the film), would regularly get women in his employment to “twirl” for his enjoyment, mandated them to wear short skirts on air and even convinced one terrified employee (when alone with him in his office) to raise her skirt bringing her to tears. The film cleverly uses a fictional character, Kayla Pospisil, to represent stories that had been told to by a number of female Fox news staff members and their experiences with Ailes over a number of years. As writer of the film Charles Randolph states “What happens inside of Roger’s office is based on the stories of three women we had access to.” In one interview Lithgow admitted the difficulty of finding humanity in a character like Ailes and said he had to “plumb the depths…and look for what makes that person tick, not to exonerate him but to explain him’. Ailes he explains ‘carries this terrific guilty secret’ and one can imagine it was something he feared being exposed. Eventually, Fox News settled a $45 million settlementfigure with those making allegations against Ailes and insisted upon his resignation. Quite unbelievably this resignation came with a $40 million pay off for Ailes himself who died a year later never having experienced any kind of real punishment for his crimes other than to be forever remembered as a predatory boss. 

90. Ron Carlisle, (Tootsie, 1982)  

“You don’t like me, do you? Now, I can respect that. There’s not many women that I can’t make like me. Why don’t you like me?”

Sydney Pollack’s Tootsie is a film about an aspiring , out of luck actor, Michael Dorsey (played by Dustin Hoffman). Failing to find work due to his reputation as a difficult actor in the business he takes radical measures and decides to dress up and audition for a TV show as a woman, Dorothy Michaels. Ron Carlisle, played by Dabney Coleman, is the sexist director of the TV show who treats women in his employment as commodities, objectifying them in a variety of ways through his language and his expectations to be the object of desire. Whilst the film is very funny, it has a deeper dark points to get across about the entertainment industry and wider society.  In one extremely emotional interview Hoffman explained why “[Tootsie] was never really a comedy for me”. Openly shedding tears of shame he explained how dressing up as Dorothy and having people judge whether he was beautiful enough to pass for a scene made him reflect about his own behaviour in the past. He might not have spoken to a woman at a party, for instance, because they were not especially beautiful, he explains: “there are too many interesting women I have not had the experience of knowing because I was brainwashed.” He believes the film Tootsie is most valuable because it highlights the sheer pressure that women are under to look a certain way and live up to a certain standard of beauty. And it explains (or at least reflects) the shallow misogyny and toxic masculinity of characters like Ron Carlisle and the way directors in particular look at and prey on actresses using them as objects to illuminate scenes or not. More interesting still, Hoffman’s honest and tearful admission perhaps provokes us to reflect on our own capacity to sometimes do this ourselves – to unfairly judge a book by its cover – in the workplace and our everyday lives. 

Identity Ten: The Good Boss 

There have been some pretty awful bosses explored in the blog so far – wonderful characters, but awful nonetheless. But alas, all is not lost. There are some positive portrayals of management in TV and film which are there to give us all hope and something to aspire towards. There are some good bosses. “Good” is clearly a normative term – what is good for you might not be good for me – but this managerial identity is more concerned with the manager being ethically sound towards their staff and being on the side of good (of wanting to preserve justice, honesty, working together as opposed to corruption and injustice). In many respects, it reflects the recent Taylor report in to “Good work” which explored workplaces that were trying to preserve decent working and management practices. In 2018 Comparablyreleased results of a huge anonymous survey including a list of the organizations with the best managers in the USA and suggested that “[t]hese managers expressed empathy and caring for their employees as individuals. There was a key sense that they were fair in their dealings with everybody.” In many respects, that is also what these managers from fiction below reflect – they aren’t always angels (that would be a bit boring!) but they are fair in their dealings and they are perhaps signs that culturally we haven’t completely given up on the boss:

91. Tony Wilson (24 Hour Party People, 2002) 

“Factory Records are not actually a company. We are an experiment in human nature. You’re labouring under the misapprehension that we actually have a deal with, er, with our, our bands. That we have any kind of a contract, er, at all, and I’m afraid we, er, we don’t because that’s, er, that’s the sum total of the paperwork to do with Factory Records, deal with, er, their various bands.”

As this blog has shown, there is a propensity for bosses in popular culture – and indeed the real-world upon which it draws upon – to be controlling and dictatorial. It is rare to find a manager who lets go and gives freedom to their workers in what they produce and create. Autonomy is the value which I place highest in my own working life. I am incredibly lucky to be able to write about whatever I want to, with whomever I want to and to whatever time-scale I want to. I doubt this piece of writing would have been produced had I been instructed more directly from an authoritarian boss suggesting what I should be writing about Obviously there are consequences if I fail to perform but the autonomy is there about how I actually produce. Michael Winterbottom’s 24 Hour Party People is a biopic of a manager who embodies, in my mind at least, the spirit and virtue of a boss that truly understands the values of creativity and letting go of control to get the most out of people. Tony Wilson was the founder of Factory records, a central player in the Manchester music scene from the late 1970s to the early 90s. It is a comedic journey which follows Wilson (played by Steve Coogan) as he shifts the London-centric music scene northwards through signing and nurturing bands such as Joy Division, the Happy Mondays and New Order, cultivating the “Madchester” music scene. 

The film gives us an inside look at this era through the eyes of Wilson, who acts as (a potentially unreliable but humorous!) narrator. Many stories of Wilson’s actions as manager have been corroborated from numerous sources however, and reflect the kind of boss he was at a time when control was king, especially in the music industry! When Wilson signed Joy Division to Factory records he famously signed the contract in his own blood and split the profits 50/50 with the band – the kind of deal that was simply unheard of at a time when record companies were milking profits from the talent. On this dynamic he noted: “The musicians own everything, the company owns nothing. All our bands have the freedom to fuck off.” But for that very reason, they generally stayed. That is not to say that total creative freedom from a manager can’t backfire. One story reflected in the film recounts the production of the now infamous New Order Blue Monday album which the management team agreed to produce to resemble a floppy disk with elaborate markings on the cover. By the time it was rolling off the shelves Wilson and colleagues realised that they were losing money on each album they sold. Similarly with the creation of the Hacienda nightclub in Manchester which Wilson co-owned and managed. The club was one of the first to import, play and popularize house and rave music from Detroit and matched this up with the rising popularity of ecstasy, which (apparently!) complemented the music perfectly. The film reflects the sheer exuberance and feeling of the acid house craze of the 80s and 90s within the Hacienda, but also notes that it ended up over 2 million pounds in debt before its eventual closure in 1997. The important thing to learn from Wilson as a manager is in his attitude towards money and profit versus creativity. As he once tellingly remarked: “All that was valuable was the history we made, not the money that we made.” Wilson truly embodied the idea that good management is letting go of control and remembering it is about what you create together rather than how much money that you make. 

92. Michael Bluth, (Arrested Development, 2003)  

Narrator: “Michael was adjusting to his new position as vice president, which meant doing the work of the president, his brother Gob.”

Michael Bluth (played by Jason Bateman) is the son of real estate mogul George Bluth. When his father is jailed for fraud he reluctantly becomes the president/CEO of the Bluth Company. Michael is smart, hardworking, self-sacrificing and essentially a good man. The only problem is everybody else in his family is stark raving bonkers. In this sense, Michael is the glue that holds them all together and is a rare example of a manager on the screen who is the source of stability and continuity. In the comedic sense, Michael is the “straight man” and we see the world through his eyes and his point of view, helping us to see how difficult it might be for a manager to manage dysfunctional people. It is a reminder perhaps that managing people is not an easy job and often it takes the patience of a saint – particularly when it involves dealing with members of your own family. In one subtly hilarious scene Michael makes his 14 year old son George Michael manager of the family frozen yoghurt stand. His son, being told that he is “Mr Manager” takes being called this incredibly seriously, because managers are, of course, synonymous with being an adult and being in charge. George Michael and his father subsequently go on to burn the banana stand down to the music “taking care of business” in an act of (costly!) defiance that reflects the chaos of the lives that they are all living. 

93. Ted Hastings (Line of Duty, 2012)  

“For years, the security in this department has been watertight fella, absolutely watertight! Then you come along, suddenly we are leaking like a colander” 

A good boss also knows how to spot the “bad apples”,  those who are seeking to undermine the organization by consistently breaking fundamental rules. Ted Hastings (played by Adrian Dunbar) is one of the best examples of this on our screens in recent years. Hastings is a superintendent police officer in charge of the AC12 Unit – the professional standards department of Central Police. It is their task to investigate officers who are suspected to be corrupt or to be breaking the rules in some way or another. The series begins with Hastings recruiting and assembling a team of police officers who he believes have the moral fortitude and honesty to rid the force of dirty coppers. He is referred to regularly as “boss” and “gaffer” within the office by his subordinates and has total respect on the team. However, the reason why he has become such a widely loved boss on our television screens is the exasperation he shows for the people who make his job so difficult (including his own team) mixed with his sheer bloody mindedness and relentlessness to clean up the police force. He has managed to develop an almost cult-like status due to the Ted-isms that he utters on such a regular basis. In fact, so integral and amusing are his catchphrases here are a selection of some of his best lines from the show which capture the kind of man and boss that he is: 

  • “None of my team planted the evidence, they know I would throw the book at them, followed by the book shelf”
  • I don’t care if it’s one rotten apple or the whole bloody barrel”
  • “I’ve said it before and I’ll say it again. Catching criminals is tough but catching coppers…god give me strength”
  • “These charges are like Grandma’s nightgown…it covers everything”
  • [when they get a break in the case] “Now we’re sucking diesel!”

In one interview Adrian Dunbar suggests that the character of Hastings is based on  “those great Scottish football managers like Jock Stein, Bill Shankly, Alex Ferguson, plus Fulton Mackay [the actor who played prison officer Mr Mackay in Porridge]. Working-class men of moral fortitude.” He goes on to say that “people feel a lot of warmth towards Ted because his decisions have been based on doing the right thing. We like to think there are people running our institutions who have a genuine sense of civic duty, that’s the sort of thing that’s missing today, so he represents something from an older world. Ted has an old-school integrity.” It is this integrity and desire to work his hardest to defend and promote an ethical foundation within his public institution that seems to be so attractive to me and to many viewers. Inevitably, however, in recent seasons of the show, doubt has been cast on Hastings himself – whether he is in fact the mysterious and unknown “H” character that is orchestrating much of the corrupt activity within the police force. This flirtation with revealing that even Hastings is a “bent copper” is probably a reflection of a wider societal disillusionment with the bosses in our public institutions. Our deepest fear is that even those who seem to be clean and honest and decent, eventually turn out to be just as bad as the others. In this case, I hope that the final season (yet to be aired) proves Hastings to be above reproach and that he remains in my mind a good boss.

94. Maria LaGuerta (Dexter, 2006)  

Vince Masuka: “Vince Masuka only swings one way.”
Debra Morgan: “Yeah, from vine to vine…”

Lt. Maria Laguerta: Enough! Glad to see the sexual harassment seminar really paid off.”

Maria LeGuerta (played by Lauren Velez), is captain of Miami-Metro Homicide Department in the TV show Dexter which ran to much critical acclaim from 2006 to 2012. Dexter follows the titular character, Dexter Morgan, who is a bloodstain pattern analyst by day and a serial killer by night. Dexter works alongside his captain LeGuerta on a daily basis with the latter completely unaware that this talented, charming man that she manages is a violent, sociopathic killer. Whilst we learn early on that he has worked out a “code” for killing people who he believes deserve to die anyway (child killers, wife beaters etc) the TV show plays out with this tension between Dexter and his oblivious colleagues at its heart. The difficult thing about being considered a good manager is that no matter how many positive characteristics you display in your role, if you display one that is considered negative it is this which many people will focus upon. It becomes a stain or a taint upon the record meaning that consistently good managers are very difficult to find. For this reason Maria LeGuerta is a controversial choice for this section because she indeed has flaws. She is ambitious and manipulative in her attempts to gain promotion. But it is easy to understand why: she is a woman in a man’s world and has to use every advantage she has got in order to progress. 

Despite this, she also has one overriding quality that makes her a role model of a boss in my eyes: loyalty. When her colleague and most talented police officer, Sergeant James Doakes is framed and murdered, she is the only person who stands by him and devotes herself to catching those responsible – which includes Dexter himself. Eventually this search for justice and her devoted loyalty to her colleague leads her to meet a grisly end as well. On LeGuerta’s exit from the show, Velez said in one interview that it was fitting she died trying to catch Doakes’ killers: “She proved that she was willing to die for what she believed was right and what she believed was good, which was bringing down evil…we’ve always thought that LaGuerta was this manipulative political animal and she was, but at the end of the day, she wanted to be a good cop and she was a good person.” I include LeGuerta here then as an example of a good manager that was nonetheless flawed in a number of very obvious ways. A loyal boss who stands by her colleagues through thick and thin is enough as far as I am concerned to show that she was somebody I would want in my corner.  

95. Apu Nahasapeemapetilon (The Simpsons, 1989) 

 “Slap on your bullet proof vest, Sanjay. It’s time for another bank run.”

Apu Nahasapeemapetilon (voiced by Hank Azaria) in the long running TV cartoon The Simpsons is boss of the local Kwik-E-Mart in Springfield, USA. He is an incredibly hard worker, providing for his family through long hours in what is often portrayed as an extremely dangerous job. He is regularly held at gun point for cash (usually by notorious criminal “Snake”) and has to risk life and limb just to keep his beloved store and its takings safe. He appears to me to be a fully-fledged three dimensional character that whilst playing on racial and national stereotypes (often quite lazily) does bring his religion (Hinduism) and his culture to the fore on Western TV in a way that rarely happened before him. The Simpsons was a huge part of my childhood and over the years I have probably watched it more than any other TV show or film. From the hilarious musical number “Who Needs the Kwik-E-Mart?” where Apu is fired from his job and has to travel to India to try and win it back. To the episode where Apu applies for US citizenship, shining a light on just how ridiculously detailed the test was but incredibly valued it was for him to feel part of American life and culture. There are many reasons to celebrate this character that made many of us laugh He was a depiction of an Indian-American in charge and playing a role in a community that was widely respected and cherished in a way brought joy to many people.

However, it would be remiss to overlook the backlash against the character from within the Indian-American community. In 2017 Hari Kondabolu released the documentary “The Problem with Apu” which questioned both the stereotypical characterization of Apu (as a put upon convenience store manager, forced in to arranged marriages amongst other things) and the fact the character was voiced by a white man. Kondabolu said of Azaria’s voicing of the character is was like “a white guy doing an impression of a white guy making fun of my father.” The response to the documentary was so strong that Kondabolu received death threats from around the world. There was a tangible, almost hysterical fear amongst fans that this character would be cancelled and removed immediately from the show. Kondibolu did not in fact argue for the removal of Apu but for the writers to be aware of the impact that this character had had on many individuals in his community. Prominent American Indians such as Kal Penn and Aziz Ansari talked about their own experiences of being mocked with the Apu voice whilst growing up, with cries of “Come again!” (Apu’s famous catchphrase) being hurled at them regularly. Penn reflected this racist abuse quite poignantly in one scene in his otherwise incredibly funny film Harold and Kumar. So whilst there were subsequent calls to remove Apu from The Simpsons altogether Kondibolu pleaded with the makers of the show instead to write different less stereotypical stories about him and to consider how the character was voiced in future shows. 

The Simpsons own response was to say” “Hey, we stereotype everyone!” and this was accurate with depictions of Scottish, Italians and all sorts of over the top representations in search of a laugh. They even chose to write and run a whole episode exploring the issue resulting in Lisa Simpson talking directly to camera, breaking the fourth wall and glibly indicating that the writers were not going to bow to pressure and change. Indeed, not all Indian Americans welcomed the removal of Apu that many voices in wider society were now demanding. Bhaskar Sunkar wrote in the Guardian for instance about how inspiring it was to see a three-dimensional Hindi character on his TV screen during his youth and that his removal would not be a good thing. Eventually, however, it was Hank Azaria himself who forced The Simpsons’ hand declaring “my eyes have been opened” and that he was willing to “step aside” in voicing the character. Apu has not been seen within Simpsons episodes since this time.

 On one hand this is, to me and many, a sad result. Even Kondibolu never intended for the character to be removed entirely and for there to be one less Indian American representation on our screens. It was merely the suggestion that it should be considered what wider impact lazy stereotypes have on real peoples’ lives. In one fascinating video, a journalist talks to a range of younger people in downtown Mumbai, asking them to watch a clip of Apu in his managerial role and give their response as to whether it was funny or offensive, or perhaps even both. The responses are absolutely fascinating and reflect a range of opinions across the spectrum. It really highlights why it is such a difficult topic to address. Nevertheless, despite this complex debate surrounding the racial stereotypes of the character, it is undeniable (to me at least) that Apu is a rare representation of a good boss in TV and film. He was somebody within the show that was often the hero (saving Homer from his own burning home) and someone with whom we all related and sympathised with. It is a shame that a compromise could not be found and it is the last we will see of him on our screens. 

96. Monica Rawling (The Shield, 2002)  

“You were the red-headed step-child when I arrived here. I put my ass on the line to give you a second chance when nobody else would. I gave you power, I gave you respect. So keep your mouth shut before you lose both! I know this is hard, but I need you to look at the bigger picture.”

Monica Rawling (played by Glenn Close) is a captain in the Los Angeles Police Department working out of The Barn, in down-town Farmington, a particularly rough area of the city, known for gang violence, drug trafficking and prostitution. The barn has, over the years, suffered from poor leadership ranging from the corrupt to the incompetent, enabling an environment in which cops could do as they please. The central protagonist and anti-hero of the show, Vic Mackey (played by Michael Chiklis), is a corrupt police officer who will do whatever it takes to defeat criminals whilst pocketing money and drugs that he comes across in the process. Rawling enters the show in season four, and is tasked with the job of cleaning up the department and taking on Vic and his “Strike team”, which by this stage were totally out of control. One of the most difficult tasks of any boss is having to try and tame an incredibly talented loose cannon within the organization. However, through a mixture of tough love (disciplining Mackey) and courageous leadership (joining the strike team on missions) she demonstrates what an incredible boss she is throughout the season. 

Despite her positive characteristics, on occasion her decency, narrow-mindedness and naiveté allowed her to be taken advantage of within the department. The problem with good managers (and people) that they can be too trusting at times and they can believe that they have won others over when in fact they are being played. Once she had caught and arrested the “big bad” of season four, she knew her time was up and she was no longer going to be in charge of the department In an emotional scene after Rawling has been fired from her position we see her pleading with Mackey to look after himself, and we get a rare sight of how much these two people respected each other and above all, how much they care about their jobs and the pursuit of justice (albeit in very different ways). Losing her position in charge of the police department means more to her than we even realised, because she really felt she could make a difference. She was undoubtedly the best of the variety of managers we saw over the seasons. Some of the Captains were too weak and were walked all over, and others too harsh and failed to gain respect. Rawling walked the line and was the most respected of them all by Mackey and the other officers. The tears she sheds at the end of her journey in the show are reflective of how much she wanted it to work and what a decent and strong willed person she was. 

97. Andrew Jorgensen (Other People’s Money, 1991)  

“I want you to look at him in all of his glory: “Larry the Liquidator”. The entrepreneur of post-industrial America, playing God with other people’s money. The robber barons of old at least left something tangible in their wake – a coal mine, a rail road, banks. This man leaves nothing. He creates nothing. He builds nothing. He runs nothing. And in his wake lies nothing but a blizzard of paper to cover the pain. Oh, if he said, “I know how to run your business better than you”, that would be something worth talking about. But he’s not saying that. He’s saying “I’m gonna kill you because at this particular moment in time, you’re worth more dead than alive.”

Norman Jewison’s Other People’s Money is a film about the rising tide of neo-liberal capitalism and the way it conflicts and contrasts with many of the traditional values of American capitalism. The film’s main protagonist is Larry “the liquidator” Garfield (played by Danny De Vito) – a greedy, soulless business man whose job it is to swoop in on struggling companies, buy them up, strip them of assets and sell them on at a profit. Andrew Jorgensen (played by Gregory Peck) is the president/boss of Larry’s latest target New England Wire and Cable. A company which whilst struggling is holding up and employing a vast majority of people in the local area. Jorgensen is a decent, upstanding man who wants to keep running the business and decides to fight tooth and nail to keep it out of the hands of the liquidator. The only person standing between Larry and the business is a beautiful attorney, Kate Sullivan (played by Penelope Ann Miller) who also happens to be the daughter of the assistant (and companion) of Andrew Jorgensen. Somewhat predictably Larry falls in love with Kate and so is torn between his lust for “other people’s money” and his lust for Kate. The film is comedic in tone but has some incredibly powerful scenes that explore the difficulties of an old school manager (Jorgensen) committed to the values of business being connected to communities and of defending them from predatory business men. 

The high point of the film comes when Andrew Jorgensen gives an emotional speech, a plea to shareholders in a meeting in which they will vote on whether to sell the company off to Larry. It is a wonderful argument (the core of which is outlined above) in which he also states: “God save us if we vote to take his poultry few dollars and run…god save our country if that is truly the wave of the future…a business is worth more than the price of its stock!” In his review of the film Roger Ebert writes that “Gregory Peck’s words and delivery here reminded [him] of the key scenes in a lot of theFrank Capra classics, where the little guy stood up and defended old-fashioned American values, and got a standing ovation, and the movie was over.” In this case, the movie was not over. Larry gives a surprisingly powerful response: This company is dead, I didn’t kill it…it was dead when I got here.” He urges people to recognise it as so and to take the money and invest in something new, that isn’t (as he sees it) on the verge of obsolescence. The vote takes place and the people give Larry control of the company. He returns to the city but feels strangely despondent about his success. He then receives a surprise phone call from Kate saying a Japanese firm wants New England Wire and Cable to make parts for a new airbag. Seemingly changed by all of his experiences he agrees to a lunch with Kate, seemingly won over to the “good side” in what amounts to a Hollywood ending, ultimately reflecting the powerful influence of good bosses (and good people) on others. 

98. M (Skyfall, 2012)  

M: “You don’t like me Bond, you don’t like my methods. You think I am an accountant, a bean counter, more interested in my numbers than your instincts” 

James Bond: “the thought had occurred to me”

M: “Good, because I think you’re a sexist, misogynist dinosaur, a relic of the cold war. Whose boyish charms, although wasted on me, obviously appeal to that woman I sent out to evaluate you”

M is a character that has appeared in James Bond films since the very first, Dr No, in 1962 where he was played by Bernard Lee. Based on the books by Sir Ian Fleming, M is head of MI6 and James Bond’s boss for all intents and purposes. Originally the character was portrayed as an ex-Vice Admiral with a traditional ex-military demeanour and a stern personality, cold and very much to the point. In 1995, however, the producers of the seventeenth Bond film GoldenEye, decided to take the character in a slightly different direction. They cast film legend Judi Dench in the role, revolutionising and modernising the character for a new, younger audience. It shifted the role away from the grumpy old man towards an older but attractive, intelligent, analytical female boss who used her brain to outsmart and outmanoeuvre Britain’s enemies.

It is widely known that Dench’s M was based upon the former head of MI5, Stella Rimington – the first female head of the intelligent services. Indeed, Rimington has even responded to this and suggested she is more than happy that Dench is playing an interpretation of her, describing her as a “wonderful actress” but saying elsewhere that she “would rather have been a Bond girl”. The job in reality would be nowhere near as glamorous as it is in the films and Rimington even describes how awkward it could be on occasion. In one interview she explains: “People regard you with a certain degree of caution because they don’t know what you know. I remember going to a dinner shortly after I retired. I was sitting at a table with some very senior British businessmen, and the ambassador of a former Soviet bloc country. And he suddenly announced to the entire table, ‘She knows the names of all my mistresses.’” Whilst she admits that she did not, it was too tempting to keep quiet and leave them to sweat over what she did and did not know about them. I think this highlights one of the things I admire most about M and at the heart of her capacity to be a good manager. She has “invisible” power that she uses with elegance and class to ensure that her side comes out on top. 

At the heart of these films from 1995 to 2012 where Dench’s incarnation of M meets her eventual and tragic death, is the evolving relationship between her and Bond. It is very much like an employer-employee relationship at first, between a boss and a very difficult to manage (but undeniably brilliant) worker.  Dench says in one interview of the relationship, “[M] asserted herself over James Bond straight away, I think it was quite apparent that Bond and M tolerated each other.” She refuses to be another charmed lady of Bond’s but instead takes him on, and calls him out as a misogynist and lets him know that she sees him for what he is.  Despite this initial tension, Dench says “that [the relationship] has got fonder over the years” and in the final film, Skyfall, it was clear that M was a mother figure to bond. Indeed, in Skyfall other agents refer to her as “mum” and the evil genius they are pitted against mocks Bond’s motherly relationship with her, attempting to use it against them both. In one scene for instance she states as part boss, part mother: “You’ll have to be debriefed, and declared fit for active service. You can only return to duty when you’ve passed the tests, so take them seriously. And a shower might be in order.” This shift has been attacked by writers as lazily falling in to ‘oedipal’ clichés around gender stereotypes but for me this shift in M’s role (however uncomfortable) is the logical trajectory of her character and it humanises her before her final departure. 

99. Captain Raymond Holt, (Brooklyn Nine-Nine, 2013)  

“Every time someone steps up and says who they are, the world becomes a better, more interesting place. So thank you.”

There are bosses that divide workplaces and alienate individuals and groups without even trying. Thankfully there are also bosses that hold workplaces together and act as the glue that binds people from different backgrounds together in pursuit of a shared goal. Captain Raymond Holt of comedy sitcom Brooklyn 99 is a perfect example of the latter. Holt is the captain of the 99th precinct of New York, Brooklyn, and over the course of seven seasons has displayed in equal measure the two diametrically opposed sides of his character. For instance, he is a strict, professional, serious man who runs the department with an iron fist – an iron fist that is required to keep the array of oddball police officers working in the precinct in line. At the same time, he is a very kind man, loyal, devoted to these police officers each of with whom he forges a special bond. It is this balance which makes him such a fantastic boss and widely feared, loved and respected within the precinct. The bond he forges with Detective Jake Peralta (played by Andy Samberg and who refers to him on one occasion as “Captain Dad”) is at the heart of the show and is encapsulated in a scene where Peralta meets his bossfor the first time. 

The complex nature of Holt as an individual becomes even more apparent as we learn he is not only an African American Captain but an openly homosexual one, that has in the past experienced workplace abuse for both of these things. Indeed, in one episode Holt actively discourages an African American colleague, Sergeant Terry Jeffers (played by Terry Crews) from reporting a racist incident because he knows how much it might slow down or derail his career. Later, he realises that he is mistaken and merely advising an officer to take the same route that he took because he had no senior officers that would support him. Holt once again shows he is a good manager by thoroughly supporting Jeffers whilst still advising him on how to progress in his career. It is this kind of humility and balance to Holt which makes him so brilliant at what he does. The scene, recorded in 2018, was strangely prescient of events in 2020 where racism within the police force has been highlighted through the killing of George Floyd and Breonna Taylor. It was such a huge event that the writers of Brooklyn 99 took all the episodes they had written for the upcoming eight season and binned them, pledging to start again. Braugher himself is anxious about how the show will address the issue of police brutality, saying he isn’t sure how his character will feel: “It might mean that Holt is a staunch defender of the NYPD, or that he tries to burn the whole thing down. I know that he is a pragmatic man; I do know that he’s a loving, [if] robotic person. I’m anxious to see what that’s all about, and I have no idea what Season 8 of Brooklyn Nine-Nine is going to be, because everything’s changed.”

Braugher is well known for playing cops and particularly cops in charge over the years in TV shows most notably in the ground-breaking Homicide: Life on the Street. Interestingly, he suggests that the representation of cops within TV shows are highly influential over what people expect from them in real life and that TV show writers must take more responsibility for what they produce. He explains in one interview:

“I look up after all these decades of playing these characters, and I say to myself, it’s been so pervasive that I’ve been inside this storytelling, and I, too, have fallen prey to the mythology that’s been built up. It’s almost like the air you breathe or the water that you swim in. It’s hard to see. But because there are so many cop shows on television, that’s where the public gets its information about the state of policing. Cops breaking the law to quote, ‘defend the law,’ is a real terrible slippery slope. It has given license to the breaking of law everywhere, justified it and excused it. That’s something that we’re going to have to collectively address — all cop shows.”

Raymond Holt is an undeniably a fascinating and unique depiction of a police officer in a leading role. He is a complex man who has the potential to reflect a reality and an attempt to deal with reality in a way that can reach millions of people through comedy and incisive and cutting moments of drama. In the wake of the events of 2020 is an ideal opportunity for the writers of Brooklyn 99 to tell an honest and frank (but hopefully still funny!) account of policing and the horrible truths that it has to confront in modern America. 

100. Mr McMillan (Big, 1988) 

“A Boss needs to be knocked on his ass every once in a while.” 

Penny Marshall’s “Big” is a comedy-drama film about a 13 year old boy Josh Baskin (played by David Moscow). Josh is fed up of being too short – he can’t get on the best fairground rides and is ignored by taller girls. At the fairground he finds a Zoltar fortune telling machine which promises him a wish. He asks to be “big” and thinks nothing more of it. The next day he wakes in his bed to find he is now a fully grown adult (and is now played by Tom Hanks). He is chased from the house by his terrified mother and presumed kidnapped by this mysterious and unknown adult man. To support himself Josh is forced to get a job in the city and his first port of call is one of his favourite stores McMillan’s Toy Company. At first he is asked to work with computers inputting data but he through a chance encounter with Mr Mcmillan (played by Robert Loggia) he impresses the boss with his knowledge of toys and childlike enthusiasm and is promoted quite quickly to the boardroom. McMillan proves himself from the beginning of his relationship with Josh that he is an open-minded and willing to listen to anybody whatever their status within the company who feel that they can improve products, making better toys for the kids that they serve. 

In one scene Josh is in the board room of the toy company for the first time and is listening a colleague Paul (played by John Heard) pitch for a new toy that he believes will be a big seller. Josh listens on whilst playing childishly with the skyscraper robot much to McMillan’s amusement. Once Paul is finished he raises his hand and says “I don’t get it” challenging the visibly perturbed Paul. Encouraged by McMillan Josh pitches an alternative toy (a “Robot Bug”) that seems to be much more attractive of an idea leading his boss to say “Well done Josh, well done!”. Throughout the film McMillan is a not only a supportive boss encouraging innovative thinking but also displays that he too has an inner child. In one now infamous scene McMillan and Josh play “Heart and Soul’ and “Chopsticks” together on a giant toy piano with huge crowds gathering around to cheer them on. He is the rare example of a boss who rather than admonish staff for having fun he actively encourages is it both for productive reasons but also because generally he seems to be a nice guy. Bizarrely, the manager being a “nice guy” is incredibly rare in films. Instead, there is a genuine perception that managers should be serious and slightly mean rather than actively enjoying their work and allowing their workers to enjoy theirs. McMillan’s pure enjoyment of his job and willingness to hold on to his inner child is what makes him such a good boss in my eyes.

So, there we have 100 bosses from TV and Film, demonstrating the range of representations there have been over the past century. It is by no means exhaustive (obviously!). I have thought of and come across more wonderful examples during the writing of this blog. However, I hope to have captured the way that fictional portrayals of bosses are drawn from the real world and how, indeed, people watching depictions of managers on screen will flow back out in to society and culture shaping our perceptions about what it is to be a boss. I think it possible for us to become more aware of these cultural assumptions around management not with any intention of encouraging film and TV makers to change their output (as some more interventionist types might want to do) but merely to understand what kinds of implicit messages are going out to people about expectations around being a boss and being managed. It is fascinating to see the variety of ways that this has changed over the years but equally fascinating to see that many things have stayed the same. Thank you for reading – I hope you noticed many of the bosses above and learned about many that you did not know about previously. If you played the quiz then I hope you did well (post your score below if you are feeling brave!). Finally, if I have missed any prominent bosses from TV or Film then please do comment below and let me know which ones you have enjoyed seeing on screen! 

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