Jim Young – Boiler Room
While pretty much everyone in this movie is an enormous douchebag, Ben Affleck’s supporting role of Jim Young takes the douche-prize. The co-founder of a giant brokerage firm, his speech to young incumbent traders perfectly encapsulates the nouveau riche, frat boy dick hole persona Hollywood loves to project onto the men of Wall Street. Inject millions of dollars into a frat’s rush meeting, and the only difference between that and Young’s speech would be a few dozen uses of the word “bro” and a keg-stand.
Gordon Gekko – Wall Street
Economic powerhouse Gordon Gekko leads bright-eyed young Bud Fox down the dank, lucrative annals of insider trading, eventually crushing his young protégé, who is naïve enough to value human relationships over money. The epitome of an unscrupulous, cutthroat Wall Street trader, Gekko sure makes his actions seem reasonable to his investors, but if you get in his way on his race to the top, you’re going to find yourself in a world of hurt.
Patrick Bateman – American Psycho
Describing a guy who axes his coworker to death because he’s jealous of his business card as a “douchebag” is probably underselling things a little, in fairness. That guy across the hall who blares EDM at 7 in the morning – he’s a douche. Patrick Bateman is obviously a monster. But it’s not just murder that American Psycho focuses on, and Bateman’s ferocious obsession with material gain and outward appearance embody what many people assume high-powered Wall Street executives to be like, and his endless lust for increasingly meaningless designer goods firmly cements him in the “douchebag” pile. That, and his love of Huey Lewis.
John Tuld – Margin Call
Many of the men on this list are loosely based on actual Wall Street executives, or vague composites of several real people, but writer and director J.C. Chandor was certainly not shy in naming the absolute worst character in Margin Call "John Tuld" - an obvious combination of Lehman Brothers' Dick Fuld and Merrill Lynch's John Thain. For being at the top of the food chain, John Tuld doesn’t necessarily know how the toxic trading schemes orchestrated by his firm work, and in the midst of a financial meltdown he whimsically plays it off as mere market behavior, promising his employees there will be a lot of money to be made off the coming crisis…and the rest is, sadly, history.
The Duke Brothers – Trading Places
The Duke brothers are old, rich, and racist, so who better to make the ultimate call on nature versus nurture? Their overhauling of the lives of two inconsequential peasants in order to settle a $1 bet does eventually see them face justice, although if their appearance in Coming To America is anything to go by, they definitely haven’t learned their lesson about behaving in a more fiscally responsible manner. Come on guys, everyone knows that you never agree to hold money for an African prince!