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Top 20 Movies To Watch On Workers' Day

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Ignacio Weil

Entertainment - May 2nd 2025, 22:39 GMT+2

Cropped Horrible Bosses — 20. Horrible Bosses (2011)

Ah, the sweet fantasy of telling your boss exactly where to shove it — "Horrible Bosses" captures that dream and turns it into chaotic, wildly inappropriate comedy. Jason Bateman, Jason Sudeikis, and Charlie Day stumble their way through a plan to take out their insufferable employers, played to perfection by Kevin Spacey, Jennifer Aniston, and Colin Farrell. It’s like a cathartic fever dream for anyone who’s ever sat through a soul-crushing Monday morning meeting. Sure, the whole "murder" part is a bit extreme, but haven’t we all at least *joked* about it in the breakroom? | © New Line Cinema

Cropped Two Weeks Notice — 19. Two Weeks Notice (2002)

In "Two Weeks Notice," Sandra Bullock and Hugh Grant prove that even when you hate your job — or in this case, your billionaire boss — love (and sarcasm) might still bloom. Bullock plays a brilliant but overworked lawyer who finally hits her breaking point, while Grant leans into his charming, bumbling Britishness as her hopelessly dependent employer. It’s a rom-com reminder that sometimes quitting is the healthiest move you can make — especially if your boss keeps interrupting your personal life over *trivial* nonsense. Workers' Day message? Set boundaries, preferably with some witty banter. | © Warner Bros. Pictures

Cropped The Assistant — 18. The Assistant (2019)

Bleak, slow, and chillingly real, "The Assistant" isn’t here to make you laugh — it’s here to make your skin crawl. Julia Garner delivers a painfully restrained performance as a low-level assistant working for a monstrous, unseen boss at a film production company. This one captures the exhausting microaggressions, the endless coffee runs, and the suffocating silence of toxic workplaces better than just about any other film. Watching it on Workers' Day might make you want to draft your own HR complaint... or just quit and move to a cabin in the woods. | © Bleecker Street Media

Cropped 9 to 5 — 17. 9 to 5 (1980)

Before there were hashtags about bad bosses and work-life balance, there was "9 to 5." This feminist comedy classic stars Jane Fonda, Lily Tomlin, and the icon herself, Dolly Parton, in a hilarious takedown of workplace sexism and exploitation. Watching these three women turn the tables on their misogynistic boss is both a blast and weirdly still relevant decades later (because late-stage capitalism is a persistent little thing). Plus, the theme song is basically the anthem for anyone who's ever wanted to just smash the alarm clock and call in "over it." | © 20th Century Fox

Cropped Norma Rae — 16. Norma Rae (1979)

Sally Field shines in "Norma Rae," the ultimate Workers' Day movie if you’re feeling a little *ready to start a revolution.* Inspired by a real-life union organizer, the story follows Norma, a factory worker who finds her voice fighting for workers' rights in the Deep South. Field's powerhouse performance — which earned her an Oscar — reminds you that sometimes standing up to the boss isn’t just brave; it’s necessary. Watch it if you’re in the mood to throw a chair through a window or organize a protest after your fifth Zoom meeting of the day. | © 20th Century Fox

Cropped The Company Men — 15. The Company Men (2010)

If you’ve ever been blindsided by a corporate "restructuring," *The Company Men* will hit close to home — maybe *too* close. Ben Affleck, Chris Cooper, and Tommy Lee Jones star as high-flying executives who suddenly find themselves jobless, confused, and (gasp) having to live like the rest of us. It's a quiet, thoughtful reminder that the corporate ladder doesn’t just collapse — sometimes it kicks you off halfway up. Spoiler: downsizing looks a lot less glamorous without the golden parachute. Watching this on Workers' Day might make you appreciate your job... or at least your unemployment benefits. | © The Weinstein Company

Cropped Outsourcing — 14. Outsourced (2006)

Before "outsourcing" became just another dreaded buzzword in office life, *Outsourced* gave it a human face — and a surprisingly sweet rom-com twist. Josh Hamilton plays a guy sent to India to train his own replacements, and along the way, he (surprise!) finds culture shock, self-discovery, and maybe even love. It's a gentle reminder that behind every corporate decision are actual people, not just spreadsheets. Plus, it’s basically a warm hug of a movie for anyone who's ever had their job "restructured" out from under them. | © ShadowCatcher Entertainment

Cropped Sorry to Bother You — 13. Sorry to Bother You (2018)

Just when you thought telemarketing was already dystopian enough, along comes *Sorry to Bother You.* Lakeith Stanfield plays a down-on-his-luck caller who discovers a "white voice" trick (hilariously voiced by David Cross) that skyrockets him up the corporate chain... into some very weird and very dark places. Tessa Thompson, Armie Hammer, and an absolutely bonkers third act make this film a fever dream of late-stage capitalism, worker exploitation, and horse people (yes, horse people). It’s wild, it's funny, it's disturbing — basically the full Workers' Day mood board. | © Annapurna Pictures

Cropped The Devil Wears Prada — 12. The Devil Wears Prada (2006)

Sure, it’s about the cutthroat world of high fashion, but *The Devil Wears Prada* perfectly captures that universal working experience: doing soul-sucking tasks while your boss casually destroys your sense of self. Anne Hathaway’s Andy Sachs learns the hard way that "a million girls would kill for this job" doesn’t mean it won’t kill *you* a little inside. And Meryl Streep’s Miranda Priestly? She’s so iconic, she basically became shorthand for every boss who thinks sending you an email at 11:59 PM is "character building." | © 20th Century Fox

Cropped swimming with sharks — 11. Swimming with Sharks (1994)

If you thought your boss was bad, wait until you meet Kevin Spacey's Buddy Ackerman in *Swimming with Sharks.* This dark, razor-sharp satire shows a young Hollywood assistant (played by Frank Whaley) trying to survive the emotional torture of working under a full-blown tyrant. It's cruel, it's funny, and it’s basically a horror movie for anyone who's ever cried in the office bathroom during lunch. Watching this on Workers' Day might just make you hug your relatively normal boss... or at least *think* about it. | © Trimark Pictures

Cropped Erin Brockovich — 10. Erin Brockovich (2000)

If you’ve ever dreamed of sticking it to The Man *and* looking fabulous while doing it, *Erin Brockovich* is your Workers' Day watch. Julia Roberts, in one of her most unforgettable roles, plays the real-life legal assistant who, armed with sheer determination and an impressive collection of mini-skirts, takes down a giant corporation. It’s part courtroom drama, part "don’t underestimate me" manifesto, and it’s all based on a true story — which somehow makes it even more satisfying. By the time the credits roll, you’ll be ready to demand a raise... or at least a better office chair. | © Universal Pictures

Cropped Glengarry Glen Ross — 9. Glengarry Glen Ross (1992)

*Glengarry Glen Ross* is basically the cinematic equivalent of being screamed at by your sales manager for 100 straight minutes — but, you know, in a good way. With a cast that reads like a Hollywood Hall of Fame (Al Pacino, Jack Lemmon, Alec Baldwin, Ed Harris), this is the ultimate portrait of desperate men selling desperate dreams. Baldwin’s legendary "Always Be Closing" monologue alone will make you want to both quit your job and polish up your résumé immediately. Spoiler: late capitalism has *never* looked so sweaty and soul-crushing. | © New Line Cinema

Cropped The Apartment — 8. The Apartment (1960)

Long before "work-life balance" became a buzzword, *The Apartment* showed just how messy office politics could get. Jack Lemmon stars as a lowly employee lending out his apartment to philandering executives in exchange for career favors, while Shirley MacLaine captures hearts (and heartbreak) as the elevator operator caught up in the drama. Director Billy Wilder wraps loneliness, ambition, and compromise into one bittersweet package that still feels painfully relevant today. Workers' Day lesson? Sometimes climbing the corporate ladder just leads to a broken heart — and a lot of very awkward hallway encounters. | © United Artists

Cropped Clerks — 7. Clerks (1994)

Shot in black-and-white on a shoestring budget, *Clerks* is the ultimate ode to dead-end jobs and existential workplace despair. Kevin Smith’s breakout film follows Dante and Randal, two guys stuck in the slow-motion hell of convenience store life, cracking jokes about everything from "Star Wars" to chewing gum. If you’ve ever worked a minimum-wage gig where customers seem to exist purely to ruin your day, this movie will feel like therapy — or at least a good, cathartic laugh. Plus, the iconic line "I'm not even supposed to be here today!" is the unofficial motto of Workers' Day everywhere. | © View Askew Productions

Cropped American Psycho — 6. American Psycho (2000)

Sure, *American Psycho* is technically about a serial killer, but it’s also a chilling (and darkly hilarious) indictment of the soulless grind of corporate culture. Christian Bale gives an unhinged, unforgettable performance as Patrick Bateman, a man whose business card obsession is only slightly less concerning than his... extracurricular activities. In Bateman’s world, appearances are everything, emotions are optional, and humanity is a distant afterthought — kind of like your last quarterly team-building exercise, right? Watch it on Workers' Day and be grateful that your office rivalries *probably* don’t end in axe murders. | © Lions Gate Films

Cropped Monsters Inc — 5. Monsters, Inc. (2001)

Leave it to Pixar to turn the grind of 9-to-5 life into a heartwarming, hilarious adventure — with monsters, of course. *Monsters, Inc.* follows Sulley (John Goodman) and Mike Wazowski (Billy Crystal) as they clock into the ultimate corporate job: scaring kids to power their city. It's got all the office staples — bad bosses, corporate bureaucracy, ridiculous safety protocols — but with way more fur. Deep down, it's a sweet reminder that maybe there’s more to life than hitting your scare quota. Also: no movie has ever captured the chaotic stress of *one* mistake at work quite like this. | © Walt Disney Pictures / Pixar Animation Studios

Cropped Being John Malkovich — 4. Being John Malkovich (1999)

File *Being John Malkovich* under "movies that make your office job seem downright normal by comparison." John Cusack stars as a struggling puppeteer who stumbles upon a portal into John Malkovich’s actual brain — because, sure, why not? Catherine Keener and Cameron Diaz get delightfully weird alongside him, in a film that perfectly captures the surreal emptiness of corporate life and the desperate urge to escape it (even if it’s into, well, John Malkovich). It’s trippy, it’s hilarious, and it’s basically the art-house version of daydreaming at your desk for eight hours straight. | © USA Films

Cropped Play Time — 3. Playtime (1967)

If you’ve ever gotten lost in an office building so sterile it feels like a futuristic prison, *Playtime* will speak to your soul — albeit with a lot of mime and very little dialogue. Jacques Tati’s masterpiece is a comedic ballet of bureaucracy and urban absurdity, starring his iconic Monsieur Hulot. It’s a gorgeous, sprawling vision of modern life where everything (and everyone) seems hilariously trapped by technology and red tape. Watch it when you need to laugh at the sheer ridiculousness of daily life — or when you just need a reminder that humanity *will* find a way to trip over itself, even in a "perfect" world. | © Specta Films

Cropped Office Space — 2. Office Space (1999)

Few movies have nailed the soul-crushing monotony of office life quite like *Office Space.* Ron Livingston stars as Peter, a man so bored with his job that even hypnosis can't save him — leading to a glorious, passive-aggressive rebellion. Jennifer Aniston pops in to add some flair (literally), while Gary Cole’s Bill Lumbergh redefined the "world’s worst boss" archetype forever. It’s painfully funny and dangerously relatable, especially if you've ever plotted the demise of a malfunctioning printer. Watching this on Workers' Day is basically required by law — or at least, by the court of collective employee suffering. | © 20th Century Fox

Cropped Brazil — 1. Brazil (1985)

Topping the list is *Brazil,* Terry Gilliam’s gloriously bleak, visually stunning take on bureaucracy gone berserk. Jonathan Pryce plays Sam Lowry, a low-level worker lost in a dystopian nightmare of paperwork, absurd regulations, and malfunctioning tech. Throw in appearances by Robert De Niro as a rogue repairman (yes, seriously) and a labyrinthine plot that feels alarmingly familiar in today’s overcomplicated world, and you’ve got the ultimate Workers' Day watch. It’s funny, it’s terrifying, and it will absolutely make you side-eye the next form your boss asks you to fill out. | © Embassy International Pictures

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Workers' Day is meant to celebrate the spirit of labor — but let's be honest: sometimes work feels less like a noble calling and more like a slow descent into existential dread. What better way to honor the realities of office life, dead-end jobs, and the complicated relationship we have with work than by watching movies that get it? From biting satires to quietly devastating dramas, these top 20 movies to watch on Workers' Day capture everything from corporate absurdity to the search for meaning beyond the 9-to-5 grind. Grab your favorite snack, kick back, and revel in the bittersweet, all-too-relatable stories of working life.

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Workers' Day is meant to celebrate the spirit of labor — but let's be honest: sometimes work feels less like a noble calling and more like a slow descent into existential dread. What better way to honor the realities of office life, dead-end jobs, and the complicated relationship we have with work than by watching movies that get it? From biting satires to quietly devastating dramas, these top 20 movies to watch on Workers' Day capture everything from corporate absurdity to the search for meaning beyond the 9-to-5 grind. Grab your favorite snack, kick back, and revel in the bittersweet, all-too-relatable stories of working life.