Year: 2005
How Much Money He's Making: $20 million
What Will's Doing: Will Smith plays a teacher of goobers who want to slay and somehow humanizes the character using all of his considerable charms. Midway through, Hitch scolds a sweaty Kevin James for his flamboyantly bad dance moves like the "Q-Tip" and the "Pizza Maker." And it's the most hypocritical moment of his career. Big Willy literally made his name doing goofy-ass sashays. The flick contains crackling chemistry with Eva Mendes and one solid tip: the 90-10 rule, which in theory is smooth as hell, but in practice, we can personally testify is not foolproof.