Including Jonah Hill. While Mr. McConaughey is tasked with playing DiCaprio's mentor, Hill is a said to play DiCaprio's friend and confidant, who partakes in enjoying all the material excesses Belfort's enormous wealth afforded him. Hill has proved apt at playing the "friend" before, albeit in more comedic fare, so it's not like the role is out of his league. In the more dramatic settings of The Wolf of Wall Street though, whatever talents Mr. Hill has of portraying companionship are likely to be more appreciated than some of his efforts in the past.
Hill started out his career as a member of the Judd Apatow troupe, appearing in and starring in such Apatow produced films as Knocked Up, Superbad, Funny People, and Get Him to the Greek. While Hill became popular to the masses through these broad comedies, he has since built up some clout among a number of lofty auteurs. Appearing in films from directors such as Quentin Tarantino and Bennett Miller, Hill even received an Oscar nomination for his work with the latter director playing Billy Beane's right-hand man in Moneyball, a rare feat for a comedic actor as young as Hill.
Hill then must be considered as a potential nominee in the supporting field, especially considering the fact he is working with the vaunted Martin Scorsese. Scorsese has directed an astounding 20 Oscar-nominated performances in his career, starting with Ellen Burstyn (who won) and Diane Ladd in Scorsese's easily most underrated film, Alice Doesn't Live Here Anymore, and ending most recently with Mark Wahlberg's tough-guy cop performance in The Departed. Scorsese has even shown talent directing natural comedians in more serious fare as he famously did with Jerry Lewis in The King of Comedy (although Lewis was not nominated for an Oscar), so Hill is definitely in good hands.
As with McConaughey though, the ensemble cast of The Wolf of Wall Street may be Hill's biggest hindrance. For instance, it is very conceivable that votes for Hill and McConaughey could "cancel" each other out if one does not clearly stick out over the other as worthy of awards nominations. Also, with a cast that includes Jean Dujardin, Jon Favreau, and Rob Reiner, it is possible a third-party player could steal the attention from under the feet of both McConaughey and Hill.
A film fanatic at a very young age, starting with the Teenage Mutant Ninja Turtle movies and gradually moving up to more sophisticated fare, at around the age of ten he became inexplicably obsessed with all things Oscar. With the incredibly trivial power of being able to chronologically name every Best Picture winner from memory, his lifelong goal is to see every Oscar nominated film, in every major category, in the history of the Academy Awards.See more from Christopher