The Wolf of Wall Street (2013)

Based on the memoir of Jordan Belfort, a shady penny stock pusher that huffed and puffed and blew the doors off of Wall Street in the late 1980s and early 90s with his underhanded brokerage shenanigans, Martin Scorsese's The Wolf of Wall Street (2013) stars Leonardo DiCaprio as the titular wolf. When we first meet Jordan Belfort, he's a married shlub getting fired from L.F. Rothschild on "Black Monday" and having to get a job at a Long Island boiler room pushing penny stocks. But when Jordan realizes that he can make tons of money pushing garbage on anyone who'll take his calls, it's not long before he's recruited a wolf pack of fellow slimeballs including his cousin-loving neighbor Donnie Azoff (Jonah Hill) to work for his pump and dump scheme, "Stratton Oakmont." Soon enough he's defrauding investors all over the place, married to trophy wife Naomi Lapaglia (Margot Robbie), viciously addicted to quaaludes, and the number one target of good guy FBI Agent Patrick Denham (Kyle Chandler). He might be a defrauding douchebag, but Leonardo’s fine ass pays off in spades as he bares his beautiful buns in multiple scenes of lust and wonder. Whether he's boning Margot on a pile of money, getting a candle lodged in his keister, or just wandering around his penthouse after a wild orgy, this wolf can huff and puff and blow Mr. Man’s pants down! Meanwhile, in a wild scene we get to see Jonah Hill whip out a mock cock prosthetic and start jerking off at the mere sight of Margot Robbie! Mr. Man knows more about cocks than he knows about stocks, and more about baring it all than bear markets, but we'd sure like to do a little bonding with Leo after watching The Wolf of Wall Street!