The Worst Movie Bosses of All Time
We’ve all had an awful boss or two in our lives, which is why it’s no surprise that the big screen has had its share of them as well. From micromanagers and stingy jerks, to power trip bullies and master manipulators, when you see terrible bosses in movies, suddenly your work situation might not seem so bad. (One can only hope!)
We put together a list of the most awful movie bosses to remind you that even on your toughest day, it it could always be worse. Just to keep the list manageable, we stuck with more traditional bosses and left out organized crime syndicate and drug cartel overlords like Tony Montana in “Scarface,” sci-fi head honchos like Darth Vader and maniacal military generals like Colonel Jessup in “A Few Good Men.”
That being said, without further ado, we present the most awful bosses to ever grace the silver screen — and thankfully, not your office.
Miranda Priestly in “The Devil Wears Prada”
Year: 2006
Character created by: Lauren Weisberger
Acted by: Meryl Streep
Bad boss quote: “Details of your incompetence do not interest me.”
Why she's the worst: She berates her underlings, makes them fetch her dry cleaning and steak lunches, and expects the impossible (like getting her a flight out of Florida during a hurricane). Streep’s Oscar-nominated performance is cringe-inducing, especially when she makes Andrea (Anne Hathaway) screw over her colleague for an opportunity. Then again, the ending seems to indicate that perhaps her tough-love lessons are what actually helps Andy succeed. Or at least that’s what the “one thousand girls that would kill for that job” keep telling themselves.
Bill Lumbergh in “Office Space”
Year: 1999
Character created by: Mike Judge
Acted by: Gary Cole
Bad boss quote: “Oh, oh, and I almost forgot. Ahh, I'm also gonna need you to go ahead and come in on Sunday, too.”
Why he's the worst: Yeah… we’re gonna go ahead and say that Bill Lumbergh — with his smug voice and coffee mug — is more along the lines of the typical jerk boss you’ve probably encountered. And that’s what makes him so awful! He tries to bleed his employees for those extra weekend hours, while bombarding them with incessant reminders about his nit-picky rules regarding TPS reports and other mundane details. And lest we forget, he banishes poor Milton, one of his sad sack underlings, to the basement and deprives him of office party birthday cake!
Frank Cross in “Scrooged”
Year: 1988
Character created by: Mitch Glazer and Michael O'Donoghue, via Charles Dickens
Acted by: Bill Murray
Bad boss quote: 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."
Why he's the worst: Obviously, Ebenezer Scrooge is one of the all-time stingiest and cruel bosses, depriving poor Bob Cratchit of that extra piece of coal to keep warm and a full day off for Christmas. We chose to go with the modern version of the character, Murray’s Frank Cross, since it’s more relatable to today’s workplace.
Frank, who runs a television station, is as conceited as they come, and even has no problem firing someone (on Christmas Eve, no less!) just because he can. He’s also dreadful to his loyal assistant. Thankfully, a few ghosts show up to set him straight. (Side note: How great would it be if you could summon a few spirits up to pay your wretched boss a visit?)
Katharine Parker in “Working Girl”
Year: 1988
Character created by: Kevin Wade
Acted by: Sigourney Weaver
Bad boss quote: “Ugh! What a slob.”
Why she's the worst: When a secretary with a shaky job history (Tess, played by Melanie Griffith) gets the opportunity of a lifetime to work with a new mentor, a successful financial executive named Katharine Parker, it feels like a warm and fuzzy girl-power moment. That is until you find out that Katharine is even more ruthless and backstabbing than her male counterparts, as she plots to steal Tess’s ideas and take credit for them.
Bobby Pellit in “Horrible Bosses”
Year: 2011
Character created by: Michael Markowitz and John Francis Daley & Jonathan Goldstein
Acted by: Colin Farrell
Bad boss quote: 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."
Why he's the worst: The movie title says it all, and there are in fact three terrible bosses played by Farrell, Jennifer Aniston and Kevin Spacey in the film. Farrell’s Bobby Pellit is particularly egregious, though, as the boss who takes over his family business after his dad dies. He’s a psychopath and a coke fiend who wants to ruin the business so he can sell it, and he’s especially horrible to Kurt (played by Jason Sudeikis), who he orders to fire all the fat and disabled people in the company. He’s essentially a walking EEOC complaint.
Franklin Hart, Jr. in “9 to 5”
Year: 1980
Character created by: Patricia Resnick and Colin Higgins
Acted by: Dabney Coleman
Bad boss quote: “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!”
Why he's the worst: This character totally deserves the full wrath of the Me Too movement for his terrible treatment of female workers — if he wasn’t a fictional character, that is. He exploits them, threatens to fire them, chooses to promote men over women just because, and takes every opportunity to makes lewd remarks and spreads false rumors about their sex lives. Hart is the classic office snake, and sadly, it turns out he’s not too far removed from reality.
Blake in “Glengarry Glen Ross”
Year: 1992
Character created by: David Mamet
Acted by: Alec Baldwin
Bad boss quote: “You certainly don't, pal, 'cause the good news is — you're fired. The bad news is — you've got, all of you've got just one week to regain your jobs starting with tonight.”
Why he's the worst: It’s an iconic scene in which a real estate consultant is sent in to light a fire under a struggling sales team, and Baldwin’s Blake does just that by taking on just about the worst boss persona imaginable. He belittles their skills, mocks the cars they drive and threatens to take away their livelihoods if they can’t deliver. “The first prize is a Cadillac Eldorado. Second prize is a set of steak knives. Third prize is you're fired. Get the picture? You laughing now?” How’s that for motivation?
Jordan Belfort in “The Wolf of Wall Street”
Year: 2013
Character created by: Jordan Belfort (The movie's based on his life)
Acted by: Leonardo DiCaprio
Bad boss quote: “Sell me this pen!”
Why he's the worst: On the surface, DiCaprio’s Belfort might seem like the best boss ever, at least to the young guys lined up to work for him. His entire boiler room team makes a small fortune and gets to party with drugs and prostitutes. It doesn’t exactly make for a healthy workplace culture, but even worse — it was all fueled by fraud, money laundering and illegal scams.
Gordon Gekko in “Wall Street”
Year: 1987
Character created by: Stanley Weiser and Oliver Stone
Acted by: Michael Douglas
Bad boss quote: “If you need a friend, get a dog.”
Why he's the worst: If DiCaprio’s character was the embodiment of Wall Street greed, Douglas’s Gordon Gekko was his forefather. His famous line, “Greed, for lack of a better word, is good,” pretty much sums up the corporate raider’s philosophy on life, and he passes that on to the young stockbroker (Charlie Sheen) who idolizes him. Let’s just say it all catches up to them and things don’t end well.
Claire Dearing in “Jurassic World”
Year: 2015
Character created by: Michael Crichton
Acted by: Bryce Dallas Howard
Bad boss quote: “Lowery, man up and do something for once in your life!”
Why she's the worst: Apparently the dino theme park operations manager, played by Howard, never heard the term “work-life balance” before. When her brothers come to visit the island, she can’t be bothered, and instead, forces her assistant to be their glorified babysitter. That’s because she’s the stereotypical ice queen boss who’s so revenue-focused that she doesn’t stop to consider that her “product” might break free and eat people… until it actually does.
Margaret Tate in “The Proposal”
Year: 2009
Character created by: Peter Chiarelli
Acted by: Sandra Bullock
Bad boss quote: “Listen carefully Bob. I didn't fire you because I felt threatened. No. I fired you because you're lazy, entitled, incompetent and you spend more time cheating on your wife than you do in your office.”
Why she's the worst: Harassment in the workplace is bad enough, but imagine having a boss force you into marrying her in exchange for a promotion so she doesn’t get deported? That’s the plot of this film, and Bullock plays the cutthroat boss loathed by all so well that you actually believe Andrew Paxton (Ryan Reynolds) would be desperate enough to go along with it.
Buddy Ackerman in “Swimming with Sharks”
Year: 1994
Character created by: George Huang
Acted by: Kevin Spacey
Bad boss quote: “Look, I know that this is your first day and you don't really know how things work around here, so I will tell you. You have no brain. No judgement calls are necessary. What you think means nothing. What you feel means nothing. You are here for me.”
Why he's the worst: If you ever wanted to see a real “boss from hell,” look no further than Spacey’s Buddy Ackerman in this lesser-known film. He gets his kicks from insulting, humiliating and abusing his personal assistant (played by Frank Whaley). How would you like to see this on your employee evaluation: “You are nothing! If you were in my toilet I wouldn't bother flushing it.” Ouch!
The Duke Brothers in “Trading Places”
Year: 1983
Characters created by: Timothy Harris and Herschel Weingrod
Acted by: Don Ameche and Ralph Bellamy
Bad boss quote: “We took a perfectly useless psychopath like Valentine, and turned him into a successful executive. And during the same time, we turned an honest, hard-working man into a violently, deranged, would-be killer!” — Randolph Duke
Why they're the worst: Two old millionaire brothers, aka the Dukes, literally ruin an employee’s life as part of a small wager. The gist: They frame their white, Harvard-educated loyal employee (Dan Aykroyd) and send him to jail while they get a poor, black con man (Eddie Murphy) to take his place as part of a social experiment. If that’s not bad enough, the plot reveals that their riches were ultimately built on shady deals and insider trading.
Professor Callahan in “Legally Blonde”
Year: 2001
Character created by: Amanda Brown
Acted by: Victor Garber
Bad boss quote: “Let the bloodbath begin.”
Why he's the worst: Creepy perv boss alert: Garber’s character Professor Callahan, who also heads up his own law firm, dangles a prestigious career opportunity in front of Elle Woods, his talented law student who is also one of his interns. But as it turns out, he wasn’t really mentoring her — it was all a pretext for him to make sexual advances. And after Reese Witherspoon’s Elle calls him out on it, he doesn’t even try to deny it. He arrogantly says, “I’m a man who knows what he wants.” Ick!
Meredith Johnson in “Disclosure”
Year: 1994
Character created by: Michael Crichton
Acted by: Demi Moore
Bad boss quote: “Poor Sanders. You have no idea what you're up against — as usual.”
Why she's the worst: Yes, sexual harassment seems to be a recurring theme in our horrible boss list, and Moore’s Meredith Johnson shows that sometimes men are the victims. As a top exec, she puts her ex-boyfriend, computer specialist Tom Sanders (played by Michael Douglas), in a precarious workplace predicament — she tries to seduce him even though he has moved on and married someone else. But when he files a complaint against her, she turns the tables on him, claiming he was the perpetrator.