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Went through one of those days with a lot of stupid meetings, a crap boss, or a printer that simply didn’t work? Don’t worry, you’re not the only one, and Hollywood has been taking potshots at you for decades. This is the true definition of workplace comedy movies: it’s simply a way to get the frustrations of working life onto the screen and let you laugh at them. Here are 5 of the best to get in line tonight.
Quick Facts
| Movie | Year | Best For |
| Office Space | 1999 | Cubicle workers everywhere |
| The Devil Wears Prada | 2006 | How to survive a toxic boss.How to survive with a toxic boss. |
| Horrible Bosses | 2011 | It takes a lot of energy to burn down. |
| The Intern | 2015 | Work-life balance pick-me-up |
| Clerks | 1994 | Service and retail workers are not part of the list. |
For the Office Worker Who’s Had Enough
Office Space (1999) is the quintessential hilarious office movie that is even more relevant today. On top of his already overbearing boss, useless TPS reports, and the overall soul-destroying experience of life in corporate cubicles, software programmer Peter Gibbons is quickly reaching his breaking point. So he no longer cares at all. It’s a ridiculous and yet a very satisfying outcome. This film was made for anyone who’s ever dreamed of using a baseball bat to break an out-of-control printer.
Horrible Bosses (2011) moves the job-hater to darker, wilder territory. Three friends with deeply unbalanced bosses realise that they’ve had enough. It’s brisk, hilarious and elevates workplace burnout to a comedy show. The point being exaggerated: No matter how bad your actual boss is, these three are even worse.
For Anyone Dealing With a High-Pressure Environment
One of the hottest workplace comedy films ever is The Devil Wears Prada (2006), about the price of ambition. A young journalist finds herself as an assistant to the ruthless, icily demanding fashion magazine editor Miranda Priestly, and is soon made aware of the cost of fame. The fun is in the high fashion tyranny’s absurdity being played out in excruciating detail. Also, it’s one of the most self-aware movies about vanishing.
For a Feel-Good Reset
Not all work films have to be politically correct. If The Intern (2015) isn’t one of your favourites, it’s the most heartwarming and surprisingly moving palate cleanser on this list. Robert De Niro stars as a stressed-out, young CEO (Anne Hathaway), who hires a 70-year-old retired man (De Niro) as a senior intern to run his chaotic web-based startup. Unlike other office comedy flicks, this one subtly celebrates human interaction and a healthy work-life balance. Enjoy it when you’re in need of some reminders that work is not a battleground.
For the Service Worker Who Gets It
Clerks (1994), the film shot in black and white, for close to nothing, and totally unedited. This indie horror film from Kevin Smith is about one extremely average turn in the life of a convenience store cashier and his next-door video-store neighbour. The sense of humour is in the particular and the tedious, the absurd demands and expectations of customers, the philosophical debates, and the absolute lack of control of your own time. This is a service and/or retail position with a difference.
FAQs on Workplace Comedy Movies
What is the company’s best comedy film to watch for a movie night?
Office Space, The Devil Wears Prada, and Horrible Bosses are crowd pleasers that will appeal to most viewers. If it’s a lighter, feel-good read you’re looking for, The Intern is the one for you.
What comedy movies about work are best for those who have an uncool boss?
The Devil Wears Prada and Horrible Bosses are the most cathartic movies for anyone who’s struggling with a difficult—or unreasonable—manager; both take the situation and bring it to extremes.
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