Unless you are a professional athlete or a giant movie star, work is hell, particularly if you’ve got a jerk for a boss. That is true for virtually everyone, unless you are one of those people who just lives to work and would happily be in the office 100 hours a week. In which case you probably aren’t reading this, considering it would just dip into the time you would rather use being productive and making two or three more sales. If that’s the kind of person you are, chances are you wouldn’t mind working for any of the people on this list, because you’re either the boss, or the boss’s primary peon. But if you’re not that person, and we’re assuming you aren’t, then you can sympathize with the rest of us who have the boss from hell, and take solace in the movies that show just how awful bosses can be.
Bill Lumbergh – Office Space
The movie Office Space is pretty much designed with you, the viewer in mind, and purposely makes the boss character a passive aggressive jerk who you in no way, shape or form could ever sympathize with. Mike Judge knows that when you work in cubicle hell, chances are you are going to hate your boss for many of the various reasons pointed out throughout the running time of the movie. Lumbergh is the boss who will always corner you to try to get you to work on the weekend, without overtime, and gets on your case whenever your TPS reports might be slightly off, whether or not you’ve already corrected the mistake. As played by Gary Cole, he’s a boss we love to hate.
C. Montgomery Burns – The Simpsons
Where do we even begin with Charles Montgomery Burns? Clearly modeled, at least in part, after the next person on our list, he’s also a portrait of the evils of corporate America. He’s greedy and power hungry, and he crushes the dreams and aspirations of his underlings at every opportunity. He’d love nothing more than to have the town and citizens of Springfield under his thumb, and he’ll go to James Bond villain-like lengths to try to make that happen. For God’s sake, the guy built a machine to try to block out the sun. If that’s not straight out of a James Bond villain’s arsenal, we don’t know what is.
Ebenezer Scrooge – A Christmas Carol
Come on, how could we do a list of bad fictional bosses and not include the most notoriously horrible, thoughtless boss ever written? He comes in at number three not because he wasn’t the worst boss, but because he didn’t remain a horrible boss. If only he’d stayed on that dark, douchey path he would have easily come in at number one, but alas, the old dude had to go and grow a conscience. The penny pinching miser at the center of A Christmas Carol hates the holiday and loves money, and goes out of his way to make sure he gets as much of it as he can while barely paying his employees and trying to shatter every ounce of happiness they’ve got.
Ari Gold – Entourage
Ari Gold, made famous by Jeremy Piven in the HBO show Entourage, is perhaps the world’s largest jerk. We love watching him tear into people and realize that, if he’s on your side and fighting to get you a bigger contract, there’s no one you’d rather have on your side. But that doesn’t mean he’s a guy we would ever really want to spend a significant amount of time around, particularly in the workplace. He’s fiery, he’s aggressive and he’s remarkably vulgar, and he isn’t shy about ripping into and humiliating his employees or firing them on the spot. He’s great to watch, but man, they couldn’t pay us enough to work for him. It just makes us respect Lloyd all the more.
Les Grossman – Tropic Thunder
And here’s another guy who has taken a page straight out of the Ari Gold handbook for how to be equal parts ruthless boss and egomaniacal prick. Played by Tom Cruise in an absurd amount of makeup in the hit film Tropic Thunder, Les Grossman is a powerful Hollywood movie mogul whose company is financing the film within the film. He’s merciless when he deals with his underlings, seeing them as little more than ants to be squashed if they happen to catch him on a bad day which, unfortunately for them, is pretty much every day. His minions suck up to him and all he does in return is remind them over and over that a retarded monkey could do their jobs.
Michael Scott – The Office
Okay, so unlike the rest of the people on this list, at least Michael Scott means well and is, for the most part, a decent human being. But at the same time, he’s got to be one of the most incompetent bosses we can imagine. Given the job after a long and successful track record in sales, Michael tries harder to make people laugh and have them like him than do well at his job, and his total lack of awareness and tact cause him to say and do inappropriate things constantly. Special mention here should also go to David Brent, the boss from the original version of The Office, who is every bit as incompetent as Michael Scott and manages to make people even more uncomfortable than his American counterpart.
Miranda Priestly – The Devil Wears Prada
At first we were not going to include Miranda Priestly on this list, mainly because we would never, ever want to openly admit we’ve seen the movie The Devil Wears Prada. But, and there’s really not too much shame in admitting this, we actually have and we know very well that Miranda Priestly is, in fact, be the devil of which the title refers. Played by Meryl Streep, Miranda Priestly is one of the most impossible bosses we could ever imagine working for. She’s excessively demanding and arrogant, she’s demeaning, and she makes requests that almost literally cannot ever be fulfilled, such as getting a copy of the new Harry Potter book before it’s actually come out. Also, we totally watched this movie because Anne Hathaway is hot. Yeah, that’s it. Did you buy that?