14. The Wolf of Wall Street (2013)

It’s still pretty hard to believe Leo didn’t win the Oscar for his performance as con-artist and criminal Jordan Belfort. He shines here in one of his all-time great roles, bringing a charisma to a character Scorsese doesn’t ask you to empathize with, but does want you to understand. Scorsese’s 3 hour maximalist take on white collar criminals is a fascinating study in how someone can both loathe their subject matter and simultaneously glorify them. It’s also funny as hell, especially for a Scorsese film as the escalating absurdity only raises the stakes and interests. Scorsese tackles crime films a lot, it’s kind of his thing (Babe Ruth is to baseball as Scorsese is to crime films), but with The Wolf of Wall Street he’s able to tackle old ground in a refreshing and new way. It all combines for one of his strongest efforts to date.