10 Horrible Movie Bosses

In honor of the upcoming dark comedy, Horrible Bosses, we thought we’d look back at some of cinema’s most notoriously awful big cheeses. Some of them might even surprise you!

Franklin Hart Jr., Nine to Five

Franklin Hart thought he could still get away with womanizing, abuse and sexual harassment. He thought he was Don Draper, but he wasn’t Don Draper. He was Dabney Coleman. And he was at least two decades too late.

Buddy Ackerman, Swimming with Sharks

Buddy will backstab, insult and sell you out. Buddy will torture for his own amusement, deny you your most essential rights as a human being (such as urinating or eating lunch) and fire you when you are working at your hardest on his behalf. He sees politeness as weakness and treats kindness with disdain. And he will only respect you if you pull a gun in his face and beat him with it. Come to think of it, maybe Buddy’s not so bad. At least the guy has a code.

Bill Lumbergh, Office Space

I’ve worked for guys like Lumbergh before. They float around clueless, watching over your shoulder, because they are bored to death. They will half-listen to your concerns as they check the time on their watch. But Lumbergh has the ability to take it to another level, torturing poor Milton, passing the buck to accounting, not giving a hoot that the poor fella is working next to a boiler and quite possibly not even getting paid. Lumbergh is weak when confronted, but he is smooth just until.

Jeff D. Sheldrake, The Apartment

You would think it would be beneath a superior like Sheldrake to borrow C.C. Baxter’s (his employee) apartment so he could have an affair with some young chippy in the office. But, no, Sheldrake practically makes a sport of it. You’d think he’d check into a hotel like every other scumbag. But using his administrative assistant’s apartment makes more sense when you think about it. It’s cheaper and probably more discreet (if C.C. knows what’s good for him). Even Ms. Kubelik, whom C.C. has a crush on, isn’t safe from the man. He’s a smug one too, that Sheldrake. Disingenuous, irresponsible and apathetic, Sheldrake is a real smarmy ass.

Dr. Evil, The Austin Powers Movies

Imagine being Number 2. You’re named after a toilet deposit and your whole life, even when you had Rob Lowe-good looks, you’ve been lackey to one of the biggest morons in evildom. You’re smarter than him and you’re probably more evil than him (you know Dr. Evil found a way to cheat on those evil tests). But there you are, in the Number 2 spot, full of lofty expectations. Your employees are a bunch of anonymous henchmen who you suspect have grown up on a diet of paint chips. And yet despite all of this you have remained loyal while Dr. Evil was incapacitated. You have turned his evil empire into a resounding billion-dollar success. You get none of the praise and all the blame. And the problem with Dr. Evil is that he doesn’t recognize this. He doesn’t know his own employees. He hasn’t properly audited his departments of evil. And he doesn’t hold himself up to the same standards he holds for everyone else. He assumes everything will go according to plan despite a history of virtually nothing going to plan. He makes Number 2 wear an eye patch even though the guy has 20/20 vision and humiliates him with a beach volley ball. He sinks as low as to appear on Jerry Springer (there’s “new money” for you). He’s a terrible father to both his clone and biological son. He doesn’t even flinch when they handle loaded weapons. His ideas are stale and unoriginal and he is clueless when it comes to demanding a proper ransom. A good general listens to his advisers but Dr. Evil never listens to the good, reasonable and sound advice by those who only want to see him succeed. He is often a laughing stock amongst his peers, rivals and employees. Nothing works in his Evil Lair, not even the booby-trapped seats designed to punish his insolent inner circle. He isn’t on this list because he is an evil boss. He is on this list because he is an incompetent one.

Malcolm Tucker, In the Loop

Working for Malcolm is kind of like walking on eggshells if under the patch of eggshells were scores of Nile crocodiles who have been beaten with sticks and starved for weeks. Not unlike Spacey’s Buddy Ackerman, he has the aggravating ability to mercilessly destroy you with wit and sarcasm. With Malcolm, words truly will break your bones. Even capable employees like Judy Molloy aren’t safe from his wrath. WARNING: Strong language.

Katharine Parker, Working Girl

You have to say this much for Parker, she’s got cajones. She steals her secretary’s ideas and passes them on as her own. That’s pretty bad. The fact that it leads to a potentially lucrative deal for the company they work for, that would make the already (perhaps) over-achieving Parker that much more of a standout makes it worse. I’m sure Tess McGill was all for helping the team and all but getting backstabbed like that had to hurt. But the real cardinal sins Parker commits in my book?

1. Using an injury for sympathy
2. Bad fainting

Darth Vader, Star Wars Trilogy

I don’t see the benefit of being a good and loyal employee of the Galactic Empire. First of all, you kind of have to sell your soul given the fact that you are working for a body of government whose sole purpose is to enslave and consume the entire galaxy. Not even Hitler (or Jabba the Hut, for that matter) was so gluttonous. I understand it’s a Wookie-eat-Wookie world out there, though so you do what you have to do to put food on the table. But promotions are practically death sentences. Lord Vader’s expectations are completely unreasonable and his response to (what he would consider) failure — even if he accepts your apology — is, we could argue, a tad over-the-top. If you just keep your head down as some low-level tech guy or communications officer, you can at least pray some jerk-Rebel cruiser doesn’t attack you (or your superior officers) before your retirement package kicks in. That last thing you want to hear is some heavy breathing sociopath in a mask congratulating you on your promotion before warning you not to screw up like your last 17 bosses. No, thank you.

Miranda Priestly, The Devil Wears Prada

She has Vader-like expectations from her employees but I will say this for Vader: at least he wasn’t a pompous ass who was bitter because he felt he was so misunderstood. And he didn’t come packaged with all the irritating sighs and hand gestures. If Vader made a hand gesture, it probably meant your throat was collapsing. I’ll take that over hourly humiliation any day.

Dumbledore, The Harry Potter Series

I’m sorry, kids, Dumbledore is a real sick ticket. First of all, isn’t it a little odd that year after year he passed up the most qualified teacher at Hogwarts to teach Defense Against the Dark Arts (Professor Snape), simply because it amused him? Snape was born to teach Defense Against the Dark Arts. That would be like passing over  Jack Nicholson as the devil in The Witches of Eastwick or Flavor Flav as Flavor Flav in Flavor of Love. These are things you just don’t do because they are obvious to the rest of the world. Not to mention the fact that by passing up Snape Dumbledore was effectively putting children’s lives in danger. How so? Well let’s take a look at some of the primo hirings Dumbeldore made in place of Snape: Two murderers, one incompetent baboon, a werewolf, a man basically responsible for giving Lord Voldemort unlimited power and quite possibly the meanest and most miserable cat-loving freak on the face of the earth. So yeah, I think that qualifies him as a horrible boss.