You might think you have one of the worst bosses in the world, but your supervisor pales in comparison to the worst bosses to ever grace the silver screen.
Mr. Ducksworth – The Mighty Ducks
Ducksworth had one of the biggest hotshot lawyers in the greater Minneapolis-St. Paul metro in Gordon Bombay. After Bombay’s DUI arrest, Ducksworth got him out of any possible jail time and bailed out his star employee, cutting a deal with a judge to force Gordo to coach pee-wee hockey. Bombay turned around District Five and led them to the playoffs. Bombay added some muscle at the end of the season, poaching star forward Adam Banks due to a districting technicality, but unfortunately, Banksy’s dad was a friend of Ducksworth’s. Ducksworth, Banks’ dad and Bombay’s nemesis, Coach Jack Riley, cut a deal with the pee-wee league to let Banks stay with the Ducks’ main rival, the Hawks. After Bombay protested, Ducksworth fired him.
Famous asshole line: “Gordon, I’m going to make this very clear. Are you prepared to lose your job over some kids? Some game?”
Tony Perkis – Heavyweights
A former overweight, tormented child with severe daddy issues, Tony Perkis bought a fat camp with his trust fund, overtaking the former utopia for fatties and turning it into a factory of pain and suffering for overweight grade schoolers. Perkis seemed jovial and passionate at first, but soon devolved into an evil villain, trapping kids and camp workers in fitness hell, eventually being imprisoned by his minions after a six-mile hike gone awry.
Famous asshole line: “Attention campers: lunch has been canceled today due to a lack of hustle. Deal with it.”
Colonel Jessup – A Few Good Men
Besides laying power move after power move upon Lieutenant Daniel Kaffee during Kaffee’s courtroom questioning of Colonel Nathan R. Jessup, Jessup is one bad guy. He forged a phony transfer order to bail himself out of being charged with murder and ran a military operation in Gitmo that might rival the Nazis in 1940s Germany. Jessup forces one of his subordinates to forge the transfer order of a murdered marine, in turn causing the subordinate to commit suicide before he has to testify against Jessup in court. What a dick.
Famous asshole line: “You see Danny, I can deal with the bullets, and the bombs, and the blood. I don’t want money, and I don’t want medals. What I do want is for you to stand there in that faggoty white uniform and with your Harvard mouth, extend me some fucking courtesy. You gotta ask me nicely.”
Gordon Gekko – Wall Street
A wheeling and dealing Wall Street yuppie, Gekko embodied the spirit of the 1980s. He acquired publicly traded companies and got rid of the waste. He was really good at it too. He didn’t give a fuck who he had to fire when he took over a company. He took the young Bud Fox (great name) under his wing and tought him the ropes of the cutthroat world of the stock market. Mergers and acquisitions. Eventually, Bud and Gekko were at odds over Blue Star Airlines, and Bud ended up screwing Gekko out of millions of dollars. Gekko showed Fox the way, and his protégé screwed him over. But what really makes Gekko a terrible boss is that he agreed to be in Wall Street 2: Money Never Sleeps.
Famous asshole line: “Lunch is for wimps.”
Bill Lumbergh – Office Space
He is the epitome of the awful boss in the post-modern corporate world. Micromanaging constantly, condescending towards his subordinates and obsessed with doing what’s right for the company. But his view of doing what’s right for the company consists of filling out TPS cover sheets and putting up redundant banners in the office. He plays favorites in the office and steals staplers from people. Then take into account that he has no problem with making people come in on the weekend and his voice is more annoying than nails on a chalkboard. Bill Lumberg is the penultimate horrible boss.
Famous asshole line: “Is this good for the company?”
John Milton – The Devil’s Advocate
He’s the devil. No, he’s literally the fucking devil in the flesh. Al Pacino’s character of John Milton played the ultimate mind fuck on Keanu Reeves in this classic ‘90s thriller. Reeves plays a talented southern lawyer, Kevin Lomax, who has never lost a case, representing child molesters and other undesirables along the way. Milton seeks out Keanu to join his high-powered, multinational New York City law firm. Lomax soon comes to find out that there’s some truly shady shit going down in Milton’s firm and is swallowed whole into the seedy underbelly of Satan’s law practice. Lomax’s wife is driven completely batshit insane from living in New York City with you know, the devil, and eventually kills herself in front of her husband. In the movie’s climax, Milton reveals to Kevin that he is in fact his father and that Lomax is the spawn of Satan. Then Milton wants Kevin to have intercourse with his half-sister to procreate the antichrist to bring about the end of the world. Try working for that guy.
Famous asshole line: “Call me dad.”
Miranda Priestly – The Devil Wears Prada
In the realm of female-centric cinema, The Devil Wears Prada takes the cake as the ultimate girly-girl movie. Anytime a movie has Stanley Tucci playing either an in-your-face kind of gay man or an effeminate companion of the main character, you know no man with a working set of twig and berries should willingly watch this movie. Anyway, at the center of the story is Miranda Priestly, editor-in-chief of Runway magazine, the biggest fashion magazine in the world. She hires Andy Sachs, played by the sometimes tolerable Anne Hathaway, as her secretary and we see the torment that Miranda puts Andy through on a daily basis, giving her impossible task upon impossible task. Whether it’s her ridiculous daily Starbuck’s order or finding her kids a copy of the newest Harry Potter book just hours before they leave on vacation, Miranda is a real bitch. Don’t think I could make it in the New York fashion scene. Good thing I don’t want to.
Famous asshole line: “Details of your incompetence do not interest me.”
Warden Norton – The Shawshank Redemption
As if going to prison wasn’t soul-crushingly depressing enough, imagine your warden was also a corrupt, money laundering, pious murderer. Warden Norton took Andy Dufresne under his wing as his personal accountant, freeing Andy from the laundry and away from rapists that had tormented him in prison. Dufresne gained the favor of the warden by washing his dirty money, but when Andy found a break in his case that might prove him innocent, the warden had the witness murdered. Prison politics. But old Andy got the last laugh, escaping from the prison, stealing all the warden’s money and exposing his crimes within the prison, leading to Warden Norton’s suicide and the best ending to any movie ever.
Famous asshole line: “Put your trust in the Lord. Your ass belongs to me.”