5. Leonardo DiCaprio - The Wolf of Wall Street
This may come as a surprise, as DiCaprio's name seems to be a perennial on these type of lists, but for all the praise DiCaprio receives, he hasn't been all that lucky with the Academy lately (or ever for that matter). The last time DiCaprio was nominated for an Oscar was in 2007, for his role in Ed Zwick's conflict diamond flick (trying saying that five times fast), Blood Diamond. He has been involved in a number of big films with a lot of potential to get him a nomination, such as Django Unchained, J. Edgar, Inception and Revolutionary Road, but for one reason or another, it just hasn't panned out for DiCaprio. In The Wolf of Wall Street though, DiCaprio is back with frequent collaborator and cinematic legend Martin Scorsese. This is the duo's fifth outing together and as much success as their collaborations have had at the Oscars, surprisingly their cinematic adventures have only netted Mr. DiCaprio one Oscar nomination, for The Aviator (poor kid can't get a break). Despite this track record, I have a feeling The Wolf of Wall Street will be DiCaprio's best shot at the Oscar since his turn as the eccentric industrialist Howard Hughes. The Wolf of Wall Street is based on the autobiography of the same name by Jordan Belfort. Mr. Belfort was a Wall Street stockbroker in the 1990's living the high life on a pile of corruption, until it all came crashing down around his head. The film's script is being written by former Sopranos writer and current Boardwalk Empire showrunner (a show which Mr. Scorsese is an executive producer on) Terence Winter, who has shown a penchant for writing this type of material in his previous television offerings. It strikes me as the sort of "living on the edge" role that DiCaprio excels at and given that there will be no confusion to who is the lead of the film (unlike say The Departed), DiCaprio's got a good shot. It looks to be another crowded year in this category, so DiCaprio could easily be squeezed out yet again, but his name will undoubtedly be one that gets tossed around at year's end.