In The Wolf of Wall Street, Leonardo DiCaprio and Jonah Hill play two wildly successful stockbrokers who insane rise to power is matched only by their insane lifestyle. To put it bluntly, they're not nice guys, they do dirty work and they're the exact kind of "professionals" who you'd want to avoid in the real world. They're also in good company. These are the movie businessmen that we'd never want to do business with. Ever.
Patrick Bateman, American Psycho
On surface, Patrick Bateman is a fairly typical investment banker. His successful career has led to a wealthy lifestyle, a gorgeous girlfriend and a Manhattan apartment to die for. But since Patrick Bateman is the main character in a movie called American Psycho, all is not well in his brainspace. Although he's icy by day, he's lethal by night, murdering random strangers to satisfy dark urges and chopping up corporate rivals who were only guilty of having a nicer business card than him.
Charlie Meadows, Barton Fink
Traveling salesman Charlie Meadows seems like a good guy at first. After all, he's friendly, talkative and played by John Goodman. But don't stick around him too long, especially if you meet him in a hotel that may or may not be a clever metaphor for Hell on Earth. Pretty soon, there will be flames, shotguns and a massive, angry man screaming "Look upon me! I'll show you the life of the mind!" from down the hallway. You know what? Just don't go to Hollywood.
Jerry Lundegaard, Fargo
Car salesman Jerry Lundegaard isn't necessarily an evil guy, but he's a pathetic, spineless and downright idiotic moron whose schemes get a lot of innocent people killed. Jerry hires two criminals to kidnap his wife so her wealthy father can pay her ransom, giving him enough money to begin a new business venture. Even if things did go well, it's hard to imagine Jerry making his own legitimate plans work. He botches his criminal gig so hard that he shouldn't be trusted with anything.
Omni Consumer Products, RoboCop
We don't want to call out a single member of the Omni Consumer Products staff. Let's just call out the whole company. Any corporation that thinks privatizing and militarizing the police is a good and profitable idea is totally evil, but this company really overstepped its bounds when it used the body of a butchered police officer to build a cyborg police officer. Great science fiction? Sure. The kind of company that deserves your time and money? Um, no.
Daniel Plainview, There Will Be Blood
A good businessman is driven, determined and resourceful, three traits that Daniel Plainview has in spades. However, Mr. Plainview lacks certain social graces, like tolerance for fools, patience and the ability to properly care for a child. This is a man who gets results (and achieves great wealth doing so), but he's also a man whose tale ends with him babbling and nearly insane, bashing in the head of his nemesis with a bowling pin. In other words, you tread lightly around him.
Gordon Gekko, Wall Street
It's a shame that so many people have taken Gordon Gekko's "Greed is good" mantra to heart in real life because greed isn't good. Greed may be what makes you rich at first, but greed it what causes you to destroy the lives of too many people. Your greed is also what convinces your young protege to turn around and betray you. If there's one thing the movies have taught us, it's to never deal with stockbrokers in the '80s. Heck, stockbrokers at all!
Henry Potter, It's a Wonderful Life
When it comes to prototypical "evil businessmen in the movies," you don't get much nastier than Mr. Potter. The head shareholder on Bedford Falls' Building and Loan Association, he goes out of his way to keep poor families homeless and does everything in his power to take down the good-hearted George Bailey. Why is Mr. Potter such a bad guy? No reason is given. He just seems to take pleasure in hurting others. Chillingly, he remains undefeated at the end of the film.
The entire cast of Glengarry Glen Ross
A film where every single character on screen is a lying scumbag is a rare beast, which makes Glengarry Glen Ross all the more special. Played be a rogue's gallery of your favorite actors, these salesman lie, manipulate and coerce their marks (customers, technically) into buying land. Is the land actually valuable? Who knows...but you can't trust these guys any farther than you can throw them. If this movie teaches us anything, it's to be wary of anyone who wants to sell us anything.