7. The Wolf of Wall Street
The latest Scorsese/DiCaprio collaboration, The Wolf of Wall Street is based on Jordan Belfort's autobiographical book of the same name. Belfort was a corrupt Wall Street stockbroker living the high-life during the 1990's until it all came crashing down amidst an FBI investigation. Belfort's firm already served as the inspiration for one film, 2000's Boiler Room, but this officially sanctioned telling of his life is likely to travel much further with the Academy given the names involved. With a screenplay written by former Sopranos writer and current Boardwalk Empire showrunner Terrence Winter, this appears to be Scorsese going back to the Goodfellas/Casino/The Departed well that has made him a household name. Since the 2000's, Scorsese's Oscar record has been pretty impeccable (4/5, the exception being Shutter Island, on Best Picture nominees), as has the Scorsese-DiCaprio brand (3/4, Shutter Island again, on Best Picture nominees). The A-list of supporting players, including Matthew McConaughey, Jonah Hill, Jon Favreau, Rob Reiner, Jean Dujardin, and director Spike Jonze, doesn't hurt either.