At some point or another everybody has to work for The Man. The Man is our boss, and he tells us what to do, when to do it, and when we may stop. Even the most hierarchically-inclined of us bridle every now and then at the power The Man has over us. That’s probably why it’s so fun to watch bosses in movies -- the more awful they are, the more we love it -- because (unlike real life) we know at the end of the movie these bosses are going down.
Source: New Line Cinema
10. Miranda Priestly from The Devil Wears Prada
Miranda (played by Meryl Streep) is everything we don’t look for in a boss. Pushy, arrogant, demanding, belittling, high strung. And, worst of all, she surrounds herself with Yes Men who only bolster her false sense of brilliance and self-righteousness.
Yes, it’s true, Miranda never exactly goes down, so to speak. But Andy (Anne Hathaway) gives her a comeuppance when she quits, effectively sticking it to The Man (in this case, The She-Man). Sometimes it’s more satisfying to quit a job at an inopportune time than to watch The Man take a nosedive on your behalf. This is definitely the case with The Devil Wears Prada.
In the end Andy and Miranda are more or less on good terms, but Andy leaves with the satisfaction of knowing that she wasn’t permanently corrupted by the silly obsessions and superficialities her boss tried to impress upon her. Sometimes walking away from a job with your integrity intact is the best way to stick it to your boss. It’s a great stress reliever, too.
9. John Milton from The Devil’s Advocate
Source: Warner Bros. Pictures
Notice a pattern here? The Devil is, appropriately enough, often associated with those who provide us with employment and supervise said vocation. In this case John Milton (Al Pacino) actually is the Devil incarnate. It’s not a metaphor or a literary device. He’s straight up the living embodiment of Satan.
Kevin Lomax (Keanu Reeves) is a hotshot lawyer from Florida who never loses a case, and when the biggest law firm in the world recruits him to New York (which is where the evil of the world prefers to conduct its business), he’s a sucker for the prestige and the money.
It’s not likely that you’ll have to quit your job the way Kevin does, going up against Satan, suicide, and the whole messy lot. But that doesn’t mean any of us are immune from existential threats to our soul. This movie is an entertaining warning about what happens when you bend over backwards one too many times for your boss: you make the angels weep.
8. Gordon Gekko
Bud Fox (Charlie Sheen) takes on a similar kind of father-son relationship with his boss, Gordon Gekko (Michael Douglas), even if Gekko isn’t literally the devil. His credo, “Greed is good,” went on to inspire the Wall Street we have today and the worldwide economic collapse that followed. Like Milton, Gekko wants Bud to embrace his inner badness and selfishness. Unlike Kevin, Bud actually does, and only gives up the game once he’s indicted for insider trading and corruption and all those other little transgressions the SEC gets so nitpicky about.
The problem with Gekko is that he’s one of those bosses who makes doing bad things seem like so much damn fun. He’s smooth and slick and seemingly has more money than God, and it’s hard for Bud not to want a piece of it. Gekko is the boss who teaches you all the wrong lessons.
Most bad bosses get you fired or, worse, humiliate you into never leaving your job. Gekko goes five steps further: he gets Bud in prison. Greed might be good, but anal rape in prison is bad.
7. Katharine Parker from Working Girl
Source: 20th Century Fox
There are so many ways your boss can screw you over, but one of the very worst is when they take your ideas and claim them as their own. You have few options to redress this situation, and the most common of them is to bend over and take it. Katharine Parker (Sigourney Weaver) knows this and uses it to steal a good idea from her new employee, Tess McGill (Melanie Griffith). Her motto, “It’s a two-way street on my team,” turns out to mean, “I’ll use you up for all you’re worth and throw you out with the rest of the pencil shavings.”
In this case Tess gets her revenge, and it is sweet. In fact, it’s probably the best vengeance anyone has ever gotten on their bad boss in the history of cinema: she steals Katharine’s man, her job, and the last drop of dignity she had left in the hollow husk of her soul. If you can’t beat ‘em – well, try and beat ‘em. Just be reeeeally clever about it.
6. Ronny Cox from Robocop
Source: 20th Century Fox
Ronny Cox (Dick Jones) is a nightmare boss. Here’s the situation: you get blown to pieces by a bunch of criminals while trying to do your job as a Detroit police officer, you get brought back to life as a bionic man with the same face and brain in a robotic body, and then, to top it all off, your boss tries to annihilate you with the ferocious Ed 209. In an awesome bit of office politics, it’s only when Cox gets fired by his boss that Robocop is free to blow him out of the building with his expert marksmanship. Now that’s what I call affirmative action.
