29 Nightmare Movie Bosses & The Career Lessons They Taught Us

Photo: 20th Century Fox/Photofest.
There's nothing like laughing your head off at a crazed tyrant of a boss as you roll into the weekend and try to forget about your own crazed tyrant of a boss. Tomorrow marks the premiere of The Boss, the workplace-centered comedy in which Melissa McCarthy's brassy Michelle Darnell seeks the help of her former assistant, Claire (Kristen Bell), to claw her way back to the top. As expected, hilarity ensues.

There's plenty more where that came from. Hollywood has given us plenty of evil employers to jeer at, rooting for their downfalls while imagining that it's us, not Melanie Griffith, who finally scores the fancy office with a personal assistant. Forget rom-coms. Isn't it more fulfilling to see a micro-manager get their comeuppance? Don't we all wish we could do the "take this job and shove it" move? Aren't we all just one snotty memo away from cranking up the Geto Boys and bashing the office printer with a baseball bat?

From Gordon Gekko to Miranda Priestly, we've rounded up some of the worst bosses in film history. For better or worse, they've each taught us a thing or two about workplace power plays. Read on as we break it down.



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Video: Courtesy of Movieclips.
The Boss: Mr. Sheldrake (Fred MacMurray), The Apartment (1960)

The Employee: C.C. Baxter (Jack Lemmon)

The Issue: Expecting Baxter to let him use his apartment to seduce the apple of his eye, Miss Kubelik (Shirley MacLaine).

The Lesson: Tell your bosses to consult the Hilton.
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2 of 29
Video: Courtesy of 20th Century Fox.
The Boss: Franklin Hart, Jr. (Dabney Coleman), 9 to 5 (1980)

The Employees: Judy Bernly (Jane Fonda), Violet Newstead (Lily Tomlin) and Doralee Rhodes (Dolly Parton)

The Issue: Being a "sexist, egotistical, lying, hypocritical bigot" ought to do it.

The Lesson: Recruit your fellow girlbosses. Document everything.
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The Bosses: Randolph & Mortimer Duke (Ralph Bellamy & Don Ameche), Trading Places (1983)

The Employee: Louis Winthorpe III (Dan Akroyd)

The Issue: Framing an employee for theft and ruining his life out of sheer boredom.

The Lesson: Trust no-one, and avoid working for fat cats who treat humans like Legos.
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The Boss: Gordan Gekko (Michael Douglas), Wall Street (1987)

The Employee: Bud Fox (Charlie Sheen)

The Issue: Espousing "greed is good," pursuing a deal that would put Bud's father out of work, and general shadiness.

The Lesson: Don't break the law. Never betray your family.
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Video: Courtesy of 20th Century Fox.
The Boss: Katharine Parker (Sigourney Weaver), Working Girl (1988)

The Employee: Tess McGill (Melanie Griffith)

The Issue: Taking credit for Tess' work.

The Lesson: Own your work, and put ideas in writing!
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Video: Courtesy of Buena Vista Pictures.
The Boss: Sadie Shelton (Bette Midler), Big Business (1988)

The Employees: Graham (Edward Herrmann) and Chuck (Daniel Gerroll)

The Issue: Telling an employee her dress looks like a "blood clot" and being overly demanding.

The Lesson: Have a thick skin, but refuse to be treated like crap.
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The Boss: Frank Cross (Bill Murray), Scrooged (1988)

The Employees: Eliot Loudermilk (Bobcat Goldthwait) and Grace Cooley (Alfre Woodward)

The Issue: Treating employees like dirt, firing people during Christmas, and sending hand towels in lieu of a bonus.

The Lesson: Go behind his back and do what you want anyway, or just pray three ghosts will pay him a visit.
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Video: Courtesy of Columbia Pictures.
The Boss: Velda Plendor (Betty Thomas), Troop Beverly Hills (1989)

The Employee: Annie Herman (Mary Gross)

The Issue: Threatening banishment to Kmart, being a miserable bully, and ordering Annie to participate in Wilderness Girls espionage.

The Lesson: Don't sink to his/her level.
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Video: Courtesy of Paramount Pictures.
The Boss: Rachel Phelps (Margaret Whitton), Major League (1989)

The Employees: The Cleveland Indians

The Issue: Sabotaging the team so she can score a transfer to warmer climes.

The Lesson: If your boss has low expectations and wants you to fail, pull up your bootstraps and prove him/her wrong.
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Video: Courtesy of Warner Bros.
The Boss: Frank Shirley (Brian Doyle Murray), National Lampoon's Christmas Vacation (1989)

The Employee: Clark Griswold (Chevy Chase)

The Issue: Giving out jam subscriptions instead of Christmas bonuses.

The Lesson: Don't spend money you don't yet have. And before you take your boss hostage, ask for a meeting with management to address your performance and raise the issue.
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Video: Courtesy of New Line Cinema.
The Boss: John Williamson (Kevin Spacey), Glengarry Glen Ross (1992)

The Employee: Shelley "The Machine" Levene (Jack Lemmon)

The Issue: Holding out on good leads, lying to clients.

The Lesson: Always be closing. And don't break into the office.
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The Boss: Bendini, Lambert & Locke, headed by Oliver Lambert (Hal Holbrook), The Firm (1993)

The Employee: Mitch McDeere (Tom Cruise)

The Issue: Working for the Mafia, murdering lawyers.

The Lesson: If an offer seems too good to be true, do a little digging.
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Video: Courtesy of TriStar Productions.
The Boss: Charles Wheeler (Jason Robards), Philadelphia (1993)

The Employee: Andrew Beckett (Tom Hanks)

The Issue: Firing an employee under false pretenses because he's gay.

The Lesson: Always stand up for yourself.
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Video: Courtesy of Miramax.
The Boss: Marsellus Wallace (Ving Rhames), Pulp Fiction (1994)

The Employee: Tony Rocky Horror

The Issue: Allegedly throwing Tony out of a window for rubbing Mia Wallace's feet.

The Lesson: Don't touch those toes.
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Video: Courtesy of Trimark Pictures.
The Boss: Buddy Ackerman (Kevin Spacey), Swimming with Sharks (1994)

The Employee: Guy (Frank Whaley)

The Issue: Bullying employees.

The Lesson: Tell 'em to take this job and shove it. Also, maybe avoid working for Kevin Spacey.
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Video: Courtesy of Warner Bros.
The Boss: Captain Dudley Smith (James Cromwell), L.A. Confidential (1997)

The Employee: Jack Vincennes (Kevin Spacey)

The Issue: Murder, corruption, you name it.

The Lesson: Sometimes the answer is right under your nose. Also,
maybe don't blurt out your suspicions to a person who might actually be the guilty party.
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The Boss: Bill Lumbergh (Gary Cole), Office Space (1999)

The Employee: Peter Gibbons (Ron Livingston)

The Issue: Laying off employees, expecting employees to sacrifice
their weekends, being nit-picky about cover sheets.

The Lesson: Hide on Friday afternoons, push HR for overtime, or just take down the company with Michael Bolton.
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The Boss: Brian (Matthew Broderick), You Can Count on Me (2000)

The Employee: Sammy Prescott (Laura Linney)

The Issue: Shaming Sammy for being a working single mom, micro-manager, philanderer.

The Lesson: Seriously, don't have an affair with the boss. Fight for a more flexible working arrangement that works for you both.
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The Boss: Daniel Cleaver (Hugh Grant), Bridget Jones's Diary (2001)

The Employee: Bridget Jones (Renee Zellweger)

The Issue: Blatant sexual harassment followed by shady boyfriend behavior.

The Lesson: Don't sleep with your boss, and shut down any mentions about your short skirt.
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Video: Courtesy of UGC-Fox Distribution.
The Boss: Collignon (Urbain Cancelier), Amélie (2001)

The Employee: Lucien (Jamel Debbouze)

The Issue: Making fun of an employee with a disability.

The Lesson: Stand up to bullies, and resort to some clever pranks if need be.
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Video: Courtesy of Universal Pictures.
The Boss: Paula (Jane Lynch), The 40-Year-Old Virgin (2005)

The Employees: SmartTech's crew, including Andy (Steve Carell) &
David (Paul Rudd)

The Issue: Making inappropriate sexual comments, playing Michael McDonald.

The Lesson: Bring in your own copy of Beautician and the Beast, for starters.
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The Boss: Miranda Priestly (Meryl Streep), The Devil Wears Prada (2006)

The Employee: Andrea Sachs (Anne Hathaway)

The Issue: Back-stabbing tyrant who asks the impossible.

The Lesson: Know when to get out.
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The Boss: Jack (Alan Tudyk), Knocked Up (2007)

The Employee: Alison Scott (Katherine Heigl)

The Issue: "Tighten up?" Hmm.

The Lesson: You do you.
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Video: Courtesy of Buena Vista Pictures.
The Boss: Chef Skinner (voiced by Ian Holm), Ratatouille (2007)

The Employee: Linguini (Lou Romano)

The Issue: Being a tyrant, using the Gusteau name for his own
devices.

The Lesson: Make yourself irreplaceable. Bringing rodents into the kitchen is probably a bad idea, though.
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Video: Courtesy of Warner Bros.
The Boss: Marty Bach (Sidney Pollack), Michael Clayton (2007)

The Employee: Michael Clayton (George Clooney)

The Issue: Corrupt as hell.

The Lesson: If our job is kind of shady, assume that the people you work with can't be trusted.
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The Boss: Barry Waterman (Steve Martin), Baby Mama (2008)

The Employee: Kate Holbrook (Tina Fey)

The Issue: There's weird, and then there's Barry.

The Lesson: Decide how much weirdness you're willing to put up with.
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The Boss: Riva (Dustin Hoffman), Chef (2014)

The Employee: Carl Casper (Jon Favreau)

The Issue: Total buttinski.

The Lesson: Keep your cool while calmly asserting your control.
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Video: Courtesy of Warner Bros.
The Boss: Martin Barrow (Craig T. Nelson), Get Hard (2015)

The Employee: James King (Will Ferrell)

The Issue: Letting his future son-in-law take the fall for his financial
crimes.

The Lesson: Don't just sign off on everything, and don't take advice from those who might want you out of the picture.
29 of 29
Video: Courtesy of Universal Pictures.
The Boss: Dianna (Tilda Swinton), Trainwreck (2015)

The Employee: Amy Townsend (Amy Schumer)

The Issue: Kinda clueless, kinda ruthless.

The Lesson: Don't take orders from someone who makes winning a promotion sound like a carnival game.
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