Year: 2001
How Much Money He's Making: $20 million
What Will's Doing: Catching his first Oscar nomination. Smith snuggles into the skin of Muhammed Ali and captures the legend's charisma, lyrical cadence and unchecked self-confidence. He beefed up for the role and forwent "Hollywood fighting" for the real deal—actually boxing with real-life, championship-caliber fighters. Outside the ring, he protests the US government wanting him to shoot Viet Cong. The role (somehow) wasn’t a commercial smash, and quibbles can be made with execution, but it reestablished Smith as a pinnacle star.