10 comedy films about toxic workplace cultures

If you want to know more about the realities of being in a toxic workplace environment, are currently in a toxic workplace or are a HR/DEI professional looking to make a change to your workplace’s culture, check out Culture Shift to see how they can help.

We’ve all unfortunately had the displeasure of being in toxic workplaces at some point in our time, whether we’ve experienced or witnessed misconduct going on. You can read about my experiences and my advice for getting through them here and here.

When we watch films, we usually watch them as a form of escapism – to escape reality and whatever problems we are going through – but many actually mirror parts of our life to a creepy and often emotional tee. Because sadly toxic workplace cultures are too common and sometimes feel too taboo to really talk about, we perhaps don’t like to admit when watching some films that we’ve been in similar situations to some extent as the characters in them who are struggling at work.

Below I’ve listed 10 comedy films that depict toxic workplace cultures that you may enjoy watching but next time will perhaps look at them a little deeper as to what is really going on beneath the surface or quite blatantly.

9 to 5

As well as being a generally iconic comedy film, 9 to 5 is also one of the best feminist films of the 20th Century. Dolly Parton, Jane Fonda and Lily Tomlin play three working women who try to overthrow their awful, sexist boss Frank Hart, played by Dabney Coleman. Behind all the belly laughs, mishaps and whoops of successful joy there are themes of bullying, sexism, sexual harassment, blackmail and embezzlement. It’s also quite progressive in that the ladies implement several new ways of working for the rest of the company that were probably unthinkable and laughable back then.

Even though things have changed since 1980, the film was relatable back then and still is now as we’ve all been there done that – well, not literally in terms of tying up and thinking of murdering your boss… right? Right?!

13 Going On 30

Jenna Rink (Jennifer Garner) may not remember or know anything about her new/older life when she wakes up in her apartment after making a wish to be thirty, flirty and thriving, but the new, older Jenna is the complete opposite of her 13-year-old self – charming, fashionable, successful, wild and above all, apparently ruthless at work. 13 Going On 30 is a real feel-good romcom but office politics at Jenna’s place of work – Poise magazine – and their rivals Sparkle show the complexities of work friendships, managerial hierarchies and people’s willingness to do anything to get ahead.

Although Jenna doesn’t know it, in her career at Poise so far, she has taken credit for a colleague’s work, unfairly dismissed staff, intimidated her assistant, given away privileged information to competitors and had an affair with another colleague’s partner. But of course her true sweet-naturedness shines through as she learns to hate her new self she’s found out about and tries to rectify her toxic mistakes.

Horrible Bosses

We’ve all had a horrible boss, but as with 9 to 5 hopefully not one we’ve wanted to murder. Horrible Bosses is an over-exaggerated comedy about three men who try and get back at their insufferable bosses. Jason Bateman’s character is manipulated and overworked by his boss (Kevin Spacey) under the pretence of getting a promotion that he doesn’t, Charlie Day’s dental assistant character is being sexually harassed and blackmailed by his boss played by Jennifer Aniston (who was reportedly based on a real, former boss), and Jason Sudeikis plays an employee at a chemical company who loves his boss – until he dies and is replaced by his incompetent druggy son (Colin Farrell).

Although this film isn’t particularly great (but is better than its sequel at least), it highlights just a small handful of examples of toxic workplace cultures that too many people face. While the majority of people would just report the incidences and/or leave their jobs, the three men come up with dramatic get-even schemes that fail but do work out in their favour in the end. It is also one of few films I can recall that has a focus on male victims of sexual harassment, showing that it does indeed happen.

Late Night

Dame Emma Thompson morphs into the British Ellen DeGeneres (called Katherine, who is also a Dame) for Late Night, a film about a show host who tries to save her dwindling figures and reputation, even though she was a once acclaimed comedienne. She hires Indian-American girl Molly (Mindy Kaling) on the basis of pretty much just that to throw the cat among the pigeons (i.e. White men), despite her lack of experience in comedy. Or TV.

Although Late Night only touched on the issue of racism which we know goes on in the media industry, it does show the amount of sexism that takes place and is very much about strong female lead characters facing off each other and adversity together, even in the face of another strong woman who wants to replace the embattled Katherine with a young male host instead.

Legally Blonde 2

Snaps for Elle Woods for facing bullying and exclusion at Harvard Law School then sexual harassment and stereotypical micro-aggressions in Legally Blonde, to unfair dismissal from a boss and company unwilling to listen to employees or change their policies and more stereotypical micro-aggressions as well as sneaky and underhand superiors and colleagues in Legally Blonde 2 – and coming out on top both times, still thinking positive and looking fabulous!

Unfortunately, lawyers and other workers in the legal sector are known to face a lot of toxic cultures where they work. From being overworked, intimidated, bullied and discriminated against, many young lawyers – particularly those who are female, LGBTQ+ and/or BAME – are made to feel regret for going down this career path. But fortunately for Elle Woods things turn around for her and her “Elle Woods Way” of doing things gets her, erm, out of the woods. Bring on Legally Blonde 3! Will Reese Witherspoon return as the new US President?

Monsters, Inc.

Mike Wazowski and James Sullivan work for and with some right monsters in Monsters, Inc. – namely CEO Waternoose and their sly and snide colleague Randall. Although Sullivan is liked by some for his fearsome reputation, Mike is often overlooked and made to feel invisible, very much like their time at Monsters University.

One aspect of toxic workplace culture that Monsters, Inc. shows is the cliques you come across at work. If you’re not friendly with or a kiss-ass towards other colleagues, your manager or with any other movers and shakers, you’re seen and treated as an outsider. Mike and Sulley represent workers who attempt to make a change from the bottom up with new, innovative ideas – well, an idea they came across by accident anyway.

Morning Glory

A film that isn’t about euphemisms, Morning Glory will remind many British viewers of the dramas that constantly surround morning and daytime TV talk shows, particularly Good Morning Britain (the Piers Morgan fiasco), This Morning (Fern Britton and Phillip Schofield’s falling out), Loose Women, Lorraine and The Jeremy Kyle Show. Morning Glory follows TV producer Becky (Rachel McAdams) as she attempts to turn around the ratings of fictional failing daytime talk show DayBreak. Rachel’s biggest task is trying to get news journalist Mike (Harrison Ford) on board as its new co-host alongside the long-suffering Colleen (Diane Keaton) who he doesn’t get along with. However she does this by effectively blackmailing him due to a loophole in his contract and he is replacing the unanimously disliked co-host Becky fired in front of everyone for his inappropriate comments.

Like Late Night, Morning Glory focuses on the ego and pride of “celebrities” and the clashes that ensue when two or more of them work together and disagree. Unfortunately it also highlights how power can exempt you from punishment in some workplaces – poor Becky may technically be in charge but she is repeatedly unable to just get rid of Mike despite his poor attitude and behaviour.

Office Christmas Party

Jennifer Aniston once again plays a “horrible boss” in Office Christmas Party, in which she tries to save her dad’s business from failing by cracking down on the company’s branches and its employees. One of the branches is run by her brother, who is a fun and carefree but quite childish and incompetent boss that everyone seems to either love, try and cover his ass or take advantage of his generosity and devil may care attitude to life and business.

Office Christmas Party ticks countless boxes of toxic workplace culture, misconduct and problematic behaviour in the workplace – and that’s even before the crazy party starts. There’s sexual harassment, drugs and alcohol intake, inappropriate and rude comments about other staff members, physical attacks on colleagues, clique behaviour and intimidation, among many others. Even the company’s uptight HR lady eventually gives in under the influence. It also highlights the problems that arise from family owned companies where the lines between personal, private and business matters are often blurred and breed too much conflict.

The Devil Wears Prada

One of the ultimate films that show what toxic workplace cultures can do to people and potentially even companies, The Devil Wears Prada is based on a novel that is in turn allegedly based on the author’s real-life experience working for Vogue under the supposed titan of a boss Anna Wintour. Following its release, many people started questioning the truth behind the story regarding Wintour’s reign and Vogue’s reputation and others admitted to relating to Andy (Anne Hathaway)’s situation at work.

The Devil Wears Prada has some of the best one-liners (e.g. “hideous skirt convention”) and speeches (e.g. the cerulean sweater burn) in almost any film that always have us all laughing out loud to and gasping at the audacity of it all (e.g. “hire the smart, fat girl”). But the harsh reality is that poor Andy’s struggles in the toxic workplace of Runway HQ is all too relatable for some. She faces constant abuse for looking and being different, is overworked and underpaid, and made to feel she has “no choice” but to do things for the sake of her career progression due to Miranda (Meryl Streep)’s whip cracking. While she feels she must change her look and outlook in order to finally be recognised and rewarded, at least her heart remains in the right place and she still tries to look out for Miranda and Emily (Emily Blunt) despite their treatment of her.

The Wolf of Wall Street

I of course had to include this film despite not viewing it as a comedy but according to trusty (ahem) Wikipedia it is a black comedy and it was nominated under “Best Musical or Comedy” at the Golden Globes, which makes sense because there are certainly elements of dark humour in it. The Wolf of Wall Street follows the rise, corruption and mighty fall of a stockbroker (Leonardo DiCaprio as Jordan Belfort) and the firm he works at.

The film depicts many incidents of beyond problematic behaviour at work and shows the potential reputational and financial damage that a business can face due to the people that work there, media attention and public image. Although what’s slightly scary is that Belfort himself says that the film downplayed his drug abuse. Nevertheless, you’d think The Wolf of Wall Street would serve as a chilling warning to businesses who know there’s plenty of misconduct going on within them and hint that their downfall could also likely become a blockbuster film one day.

And that’s my top 10! Are there comedies or even non-comedies (there are probably many of these) that you can think of to add? I did also have Elf on the originally longer list because it showed the brutality of some corporate bosses who don’t give a shit about their employees, classically giving them an ultimatum of choosing between their career and their family.

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