Played: Jack Dawson
Despite a couple of hiccups (remember The Beach?), Leo defied all odds to become one of the most successful actors in Hollywood, due in part to his collaboration with Martin Scorsese, on Gangs of New York, The Aviator and The Deprated, respectively. Along the way, he picked up two additional nominations, in 2005 (The Aviator) and 2007 (Blood Diamond). Later this year, we'll see Leo in two major releases: Quentin Tarantino's Django Unchained and Baz Lurhmann's The Great Gatsby, in which he plays the titular character.