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.
Frank Cross in “Scrooged”
Paramount Pictures / IMDB
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?)
Bobby Pellit in “Horrible Bosses”
New Line Productions / IMDB
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”
Twentieth Century Fox / IMDB
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.
Gordon Gekko in “Wall Street”
Twentieth Century Fox / IMDB
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”
Universal Pictures / IMDB
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.
The Duke Brothers in “Trading Places”
Paramount Pictures / IMDB
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”
Victor Garber (left) starred as the boss in “Legally Blonde,” with Luke Wilson and Reese Witherspoon. Metro-Goldwyn-Mayer Studios / IMDB
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!
