Top Ten Most Horrible Movie Bosses

Our bosses are the people from whom we take orders. We follow their demands, do exactly as they say, scamper around town for them, make sure not to displease them as we carry out our duties, and try not to screw up their specific coffee requirements (spitting in the cup is always a temptation). We bow at their every word to save our skin, because if we don’t kiss their ass then it’s back to the job centre for us poor saps. And some bosses, mad with the power at their immediate disposal, abuse this position of commanding superiority, us inferior employees suffering miserably from their supreme, unquestioned ruling. With all this megalomania pouring through their veins, these control-freak bastards can make for marvellous antagonists in the world of cinema, mistreating their poor workers out of boredom or sheer insanity, whether they be typical office tyrants or space-dwelling dictators. So, here is my list of the top ten most horrible bosses ever to misuse their authority on the big screen. Side note: this may or may not be influenced by Seth Gordon’s comedy “Horrible Bosses,” released July 8 in the US. Okay, it is.

10. Miranda Priestly from “The Devil Wears Prada” (2006)

This self-centred boss is a high-reigning figure in the fashion world, a harsh and cruel industry that’s generally a bit of a bitch. But you know what’s even more of a bitch than the business of vanity? That’s right: Miranda Priestly, arrogant editor in chief of Runway magazine, played magnificently by the Academy Awards’ BFF, Meryl Streep. Fitted with a sharp tongue and piercing eyes that judge and patronise, malicious Miranda spends her days unflinchingly ordering around brand new assistant Andy Sachs (Anne Hathaway), scrutinising Andy’s fashion sense, discarding the food Andy has neatly prepared for her, and being baffled as to why Andy can’t book her a flight back home when there’s a massive hurricane running rampant outside. At one point, she also demands that Andy get her the manuscript for the new, unreleased “Harry Potter” book for her two daughters in under four hours, a task that is nigh impossible. And when Andy accomplishes this impracticable chore against all odds, Miranda snidely responds, “One copy? What are my twins going to do with that? Share?” What a bitch. But damn she’s glamorous.

9. Dr. Evil from the “Austin Powers” trilogy (1997-2002)

You have to admit, when you hand in an application to work under the employment of a man whose surname is “Evil,” you are essentially asking for trouble. And while the skinhead parody of a cat-stroking Bond villain has a hundred disposable henchman killing and shooting at the click of his fingers, it’s Dr. Evil’s closest associates who he mostly pesters, mocks and occasionally murders. Who could forget that scene in the first film, “International Man of Mystery,” in which Dr. Evil has subordinate Mustafa (Will Ferrell) falling into a fiery pit through a trap door under his seat for wrecking the fur of Dr. Evil‘s cat? And when Mustafa survives the incident, Dr. Evil has him shot… several times. And what about in the second film, “The Spy Who Shagged Me,” in which he bullies Number Two (Rob Lowe) for his apparent “insolent tone,” repeatedly hurling an inflatable globe at his eye-patched face, eventually making him burst into tears. Poor Number Two! Dr. Evil’s just jealous of his hair, I guess…

8. E. Edward Grey from “Secretary” (2002)

Some bosses can be sexist pigs towards their female staff members, maybe “accidentally” brushing up against them in the corridor, or having a cheeky touchy-feely in the photocopying room, resulting in a hard slap to the face and a sexual harassment charge to boot. But peculiar attorney E. Edward Grey (James Spader) takes this a little too far with his socially awkward new secretary, Lee Holloway (Maggie Gyllenhaal). Throughout the course of this strange little movie, Grey carries out his own form of work discipline; he, much to Lee’s shock, spanks the mademoiselle whenever she makes spelling errors in files and documents, thrusting the palm of his hand against her unsuspecting buttocks with kinky fury. In one rather memorable scene, he has her slide her tights down her legs, bend over his desk, hike up her skirt, and proceeds to violently masturbate while standing behind her, promptly ejaculating onto the bottom of her blouse. And he didn’t even buy her dinner!

7. Gordon Gekko from “Wall Street” (1987)


On first glance, Gordon Gekko is a charming fellow. He’s lively, he’s sharp, he’s witty and he’s smooth, Michael Douglas playing him with a scenery-chewing charisma that would win him his one and only Academy Award for Best Actor. But if you pay close enough attention to the chatty cigar-chomper, you’ll come to realise that he’s a selfish, heartless, greedy little git who’d spit in your face if it’d get him a couple extra dimes. He’s a Wall Street player, making money by stealing information when the law won’t increase the contents of his bank account. In the film, down-on-his-luck stockbroker Bud Fox (Charlie Sheen) is taken under the wing of Mr. Gekko, Fox making a ton of dough by spying and lying, following advice from his knowledgeable and ruthless mentor. However, everything soon goes a bit tits up, Fox discovering that Gekko has deceived him in their latest deal/scam, which results in Gekko and Fox both going to jail when Fox bravely tries to take Gekko down. Moral of the story: try to get revenge on your asshole of a boss, you’ll get put behind bars along with his sorry ass. Well, damn.

6. Darth Vader from the original “Star Wars” trilogy (1977-1983)

I think we all know that Darth Vader is a merciless douche bag by this point; his vicious villainy has become an iconic piece of pop culture ever since he waltzed through the corridors of Princess Leia’s ship back in ’77, clad in his flowing cape, black spacesuit and menacing gas mask. But what about how he treats the hundreds of staff members of his precious Death Star? Well, in one famous scene from “Episode IV,” Mr. Vader has his faith questioned by Admiral Conan Antonio Motti, which apparently Vader is very sensitive about. Instead of having a reasonable man-to-man discussion about each other’s religious beliefs, Vader decides to choke the admiral from across the room, using his mental powers to strangle the man, not stopping until he is ordered to do so. I find his treatment of his employees disturbing

5. Colonel Nathan R. Jessup from “A Few Good Men” (1992)

In the army, it’s a given that your commanding officer is not going to be particularly pleasant towards you. He’ll shout at you, bark orders at you, force you to take 10-mile hikes and call you a girl. But Colonel Jessup (Jack Nicholson), the commanding officer of the Guantanamo Bay Naval Base in Cuba, takes this unpleasantness a little further, ordering “code red”s on the marines he is displeased with. What is a code red? It is a form of punishment enforced upon marines who require some discipline, for example waking them up in the middle of the night and beating them with socks containing bars of soap. And when the latest code red unfortunately ends in the death of a marine, Jessup covers up his involvement, leaving the two loyal marines who carried out the code red to be charged with murder. Y’know, I’d like to walk up to Jessup and tell him how horrible he is, but I bet he can’t handle the truth. Look, even I cringed when I wrote that.

4. John Milton from “The Devil’s Advocate” (1997)

Now, you may suspect on occasion that your son-of-a-bitch boss is a demonic being, an evil spirit whose goal it is to specifically make your life a living Hell; you may even come to suspect that he is the devil himself. But in “The Devil’s Advocate,” Keanu Reeves’ boss is in fact the devil himself, played by, who else, Al Pacino. Living under the pseudonym John Milton (a little reference to the “Paradise Lost” author there for all you intellectuals), the prince of darkness is the owner of a law firm, his true form of course unbeknownst to those around him. Unbeatable lawyer Kevin Lomax (Reeves) ends up working for Milton, making quite a sum of money in the process, Lomax only learning of his boss’ true identity towards the end of the movie, when Milton offers Lomax anything he wants. He sounds like a nice guy, no? Oh, but there’s that bit where he rapes Lomax’s wife and tries to get him to have sex with his own half-sister. Umm, dude, I know you’re the devil, but that’s fucked up.

3. Bill Lumbergh from “Office Space” (1999)

“What’s happening?” Bill Lumbergh probes his fed-up employees, coffee cup in hand, elbow on their cubicle walls, probably about to ask them to come in on Saturday morning to do some more TPS reports. “That’d be great,” he’ll most likely add at the end with an irksome tone. Lumbergh is a man who represents everything that’s wrong about corporate management, his snide, slimy and uncaring attitude making his bespectacled face very punchable indeed. He’s the vice president of Initech, a software firm filled with office drones who are sick and tired of their sickening and tiring jobs. And yet Lumbergh has themed work days, making everyone dress up in Hawaiian shirts, all the while draining their energy and overall ability to really give a hoot. Oh, and he keeps the mumbling freak-show employee Milton (Stephen Root) working for him without telling him he was let go from the company five years ago, and fixes the glitch in the computer system that previously caused Milton to still get a paycheck. And he moves him to the basement where there are cockroaches crawling about! And he steals his stapler! The swine!

2. Ebenezer Scrooge from every “A Christmas Carol” movie ever

How many movie adaptations have there been of Charles Dickens’ classic novella “A Christmas Carol”? I honestly do not know. Somebody google it! Anyway, every literate individual on planet Earth should know that the story’s money-grubbing antihero is the mega-cranky Ebenezer Scrooge, most movie versions portraying him as a cold-hearted, miserly banker of sorts in 19th century England, as he is in the beloved book. His clerk is Bob Cratchit, a penniless family man who adores Christmas, as opposed to Scrooge, who despises everything about the joyous day. Scrooge treats Cratchit badly, insults his wife, pays him poorly and has him working late on Christmas Eve. Sure, Scrooge redeems himself in the end of the story, but only after he realises he’s going to die sad and alone if he doesn‘t! Actually, the hell with it, he does deserve to die sad and alone! Screw you, Scrooge!

1. Buddy Ackerman from “Swimming with Sharks” (1994)

And now we come to the number one most horrible movie boss of all time: Buddy Ackerman, played by Kevin Spacey. Buddy is a movie mogul who hires a guy named, err, Guy (Frank Whaley) to be his new assistant, deciding to treat him like a gormless teenager would a tiny little insect. Buddy takes it upon himself to inform Guy that he’s not allowed to think, that he has no brain, that his only purpose in life is to serve Buddy’s interests, and generally make him feel like nothing. Buddy doesn’t let him have lunch, shouts at him in front of everyone, throws coffee, cupcakes and paperclips at him, steals his scripts for movies, claims they are his own, and steals his new girlfriend. And when Buddy finally fires him for no reason whatsoever, Guy freaks out, breaks into his house, ties him to a chair and proceeds to torture him for his own amusement. Amongst his torture techniques are covering him in hot sauce, paper-cutting his tongue and giving him a nasty-looking haircut. And this is why Buddy is number one: he drives his assistant so insane that the assistant goes cuckoo and tortures him in the boss’ own living room. And the haircut Guy gives him looks so bad. It’s like a street rat crawled its way onto his head and died. But yes, if you see any signs of your boss being anything like Buddy Ackerman, I’ve got one word for you: run.

Honourable mentions: Patrick Bateman (Christian Bale) from “American Psycho” (2000). At one point in this rather violent black comedy, the very murderous investment banker invites his assistant to his home and attempts to kill her with a nail gun to the back of the head. He decides against it, but still. Also, Blake (Alec Baldwin) from “Glengarry Glen Ross” (1992). He’s a very mouthy representative from a big real estate company who pays a visit to a team of real estate salesmen, informing them through verbal abuse that two of them will soon be fired, judging by their progress over the next few days. I’d love to include him in the list above (his motivational speech is brilliantly harsh), but technically speaking he’s not really a boss (the Kevin Spacey character fits that position more in the film). Still, it’s an amazing scene with an amazing character in an amazing movie.

By Stephen Watson

Leave a Reply