We've all had terrible bosses in our lives. Sometimes we may even dream about harm coming to them, but never follow through, of course! In the movies things are different and we can live vicariously with these terrible movie bosses who get what they deserve.
Buddy Ackerman, Swimming With Sharks
Buddy Akerman, played by Kevin Spacey in 1994’s Swimming with Sharks is maybe the worst boss on this list. The studio exec is an absolute monster to his assistant, Guy (Frank Whaley). When he’s not verbally berating him, he’s throwing pens and the rest of the office supplies at him. Guy has finally had enough and kidnaps Buddy, brutally torturing him as only a man at his wit's end could do.
Franklin Hart Jr., 9 To 5
9 to 5 is definitely the most classic example of getting back at your terrible boss. After dealing with Franklin Hart's (Dabney Coleman) constant sliminess, extreme misogyny, and sexual harassment, they figure out how to get revenge. Violet (Lily Tomlin) thinks she accidentally poisoned Hart, so she and coworkers Judy (Jane Fonda) and Doralee (Dolly Parton) hatch a plan to kidnap him and hold him hostage until they make some changes around the office. In the end, Hart is banished by the company to Brazil where he is kidnapped again, this time by an Amazon tribe, and he’s never heard from again.
Frank Shirley, Christmas Vacation
Frank Shirley (Brian Doyle-Murray) isn’t the worst boss on this list. In the truly classic National Lampoon’s Christmas Vacation, he’s Clark Griswold’s (Chevy Chase) somewhat typical unfeeling, strict boss. Where he goes most wrong is by denying Clark his Christmas bonus, which Clark was planning to use towards installing a pool. The never-helpful Cousin Eddie (Randy Quaid) decides it’s time to act, he kidnaps Shirley and brings him back to Clark’s house, where Shirley finally sees the errors of his ways. We can assume the Griswolds were enjoying their pool later that year, even if Eddie was there to ruin it in his flippers.
Detective Alonzo Harris, Training Day
Detective Alonzo Harris (Denzel Washington) is a big-time narcotics detective in LA in Training Day. He’s also a total nightmare for the one day that Officer Jake Hoyt (Ethan Hawke) works for him. Harris is comically corrupt, running the streets with impunity, stealing drugs and money, beating people, and even murdering them. He sets up Hoyt and in the end, tries to have him killed, but a bit of luck gets Hoyt off the hook and Harris’ past bad deeds catch up to him when he’s killed by mobsters after being outed for his corruption.
Julia Harris, Bobby Pellit, And Dave Harken, Horrible Bosses
You can’t have this list without the movie that literally calls out the bosses in the title. Plus, there is not one, but three terrible bosses in Horrible Bosses, all of whom get their comeuppance in different, satisfying ways. They are Dr. Julia Harris (Jennifer Aniston), who sexually harasses Dale (Charlie Day); Dave Harken (Kevin Spacey), who takes pleasure in tormenting Nick (Jason Bateman); and Bobby Pellit (Colin Farrell), the drug-addicted idiot son who inherits a company and makes Kurt’s (Jason Sudeikis) life miserable. Due to a misguided plan and a series of wild coincidences, Pellit ends up dead, Harken goes to jail for his murder, and Harris is blackmailed into ending the harassment.
Gordon Gekko, Wall Street
In Wall Street, Gordon Gekko, played by Oscar-winner Michael Douglas, is the kind of boss we can all loathe. A Wall St. millionaire who treats the world like his own private piggy bank, and doesn’t care how many lives he ruins in pursuit of his own greed. He convinces the eager Bud Fox (Charlie Sheen) to start breaking the law by gaining insider trading info, which leads to Bud’s downfall, but not before he takes Gekko down with him after turning over his info to the Feds.
Jordan Belfort, Wolf Of Wall Street
Like Gordon Gekko, Jordan Belfort (Leonardo DiCaprio) fancies himself a bit of an inside trader in the based-on-a-true-story The Wolf Of Wall Street. Unlike Gekko, instead of buying expensive art, he buys a lot of drugs, and a lot of women. He treats all the degenerates in his office well, but everyone else in the world horribly. He’s a debaucherous disaster of a human being, ruining countless lives before, finally, his is too.
Katherine Parker, Working Girl
Katherine Parker (Sigourney Weaver) is the prototype of the mean, unrealistic female boss of the 1980s. She ends up stealing her assist Tess’ (Melanie Griffith) ideas and tries to use them to get ahead. Until Tess gets wind of what’s going on and confronts Katherine. She tries to lie her way out of it but is caught, and fired. Meanwhile, Tess gets a promotion and promised to be a different kind of boss.
Randolph And Mortimer Duke, Trading Places
Randolph and Mortimer Duke, played by Ralph Bellamy and Don Ameche, respectively, are two brothers atop their own financial firm. Bored with their millions, they make a bet that they can’t turn an “honest hard-working man” from their firm into a “violently deranged would-be killer” while turning a “perfectly useless psychopath” into a “successful executive.” Their targets are Louis Winthorpe III (Dan Aykroyd) and Billy Ray Valentine (Eddie Murphy in one of his funniest roles). The devious bet works, but Louis and Billy Ray catch on and hatch a plan to get rich, while sending the Dukes to the poor house. The brothers beg to “turn the machines back on” after one day of trading has left them broke, while Billy Ray and Louis are looking and feeling good (and rich).
Dick Jones, RoboCop
If you’re going to give a terrible boss a fitting name, Dick Jones is pretty darn good. Jones, played by Ronny Cox (who played a good boss Beverly Hills Cop), is the head of Omni Consumer Products who ruthlessly pursues the RoboCop initiative in RoboCop. He’s a heartless psychopath who puts profits above everything, including public safety. Luckily for the rest of the world, his own company’s invention gets one opportunity to take him out and does.
Hilly, The Help
Hilly (Bryce Dallas Howard) is an entitled, racist brat who is allowed to be awful to her staff in The Help. Even in 1963, this kind of terrible behavior would have been derided by many (though not all), but by today’s standards, it’s downright horrifying. Hilly’s obnoxiousness reaches its zenith when she not only fires Minny, played by Octavia Spencer, but ensures Minny won’t work anywhere else in town. On the plus side, she does end up eating poop.
Avery Tolar, The Firm
The Firm is too often forgotten these days, but Avery Tolar (Gene Hackman) is the kind of boss that leads us to nightmares. In his heart, he seems a decent man, but he is also a corrupt philanderer, who tries to lead his new protege, Mitch (Tom Cruise), down the same path. Luckily Mitch is too smart for that and with some help, he turns the tables on Tolar, finds a way out of the firm, and keeps his law license, too!
Meredith Johnson, Disclosure
Another movie seemingly forgotten from the ‘90s is Disclosure, starring Demi Moore as Meredith Johnson and Micheal Douglas as her ex-boyfriend-turned-employee, Tom. The movie flips the script on sexual harassment in the workplace. Meredith is the aggressor and threatens every bit of Tom’s livelihood after he rebuffs her advances. When she is exposed as a conniving fraud, she loses everything. Disclosure wasn’t well received, but she’s still a terrible boss.
Bill, Kill Bill
There is nothing worse than a boss that wants to kill you, right? The Bride (Uma Thurman), is getting married, so her former employer, Bill, decides she must die. When the Deadly Vipers fail, it becomes The Bride’s mission to Kill Bill. Bill, played by David Carradine, hides with her daughter whom he has kidnapped, until The Bride finally tracks him and does what she set out to do. It’s too bad we’ll likely never see The Bride again.
Gunnery Sergeant Hartman, Full Metal Jacket
Let’s be clear here, the punishment doesn’t always fit the crime, as is the case in Full Metal Jacket. Gunnery Sergeant Hartman, legendarily played by the late R. Lee Ermey, isn’t your typical boss, he’s a ruthless and relentless drill sergeant for a group of green Marines training to go to Vietnam. His harsh treatment of them, especially Private Pyle (Vincent D’Onofrio) leads Pyle to shoot the sergeant in the latrine. Sgt. Hartman was just doing his job, but he did it a little too well and paid the price.
Warden Samuel Norton, The Shawshank Redemption
Warden Norton, played by Bob Gunton in the fantastic Stephen King adaption, The Shawshank Redemption, is a religious man, but that doesn’t mean he's not a cruel one. Among his worst sins is to use Andy Dufresne and the other inmates of his prison as labor for public works projects and pockets bribes for them, using Andy to launder the money. Andy eventually escapes with all the proof he needs to take Norton down, but Norton kills himself before he can end up in his own prison.
Dr. Chilton, The Silence Of The Lambs
Dr. Frederick Chilton isn’t a warden in name, but he is in practice. Chilton (Anthony Heald) is the director of the mental institution that houses the evil Dr. Hannibal Lecter (Anthony Hopkins). He seems to take pleasure in treating Lector poorly, thinking it makes him somehow smarter than the serial killer, but that's really just an abuse of power. While it’s hard to root for a psychopath like Lector, it’s hard not to smile after he escapes and tracks Chilton down at the end of the movie, certainly planning an extravagant meal where Chilton will be the main course.
So, the lesson here is to remember, no matter how bad your boss may be, no matter how big an idiot they are, things could always be a lot worse. Of course, that’s not to say they won’t be so bad that you’ll dream about revenge, but ultimately, it’s better to just go on vacation and forget about them for a bit.
