Tobey Maguire

Born a stone's throw from Hollywood, Tobey Maguire began acting in commercials as a boy and had his first film role in This Boy's Life (1994, with Leonardo DiCaprio). He went on to play confused and thoughtful teens in several films, including the trouble-in-suburbia classic The Ice Storm (1997, with Christina Ricci), the dreamy Pleasantville (1998, with Reese Witherspoon) and the literary campus comedy The Wonder Boys (2000, with Michael Douglas). In 2002 he had the high-swinging lead in the hit film Spider-Man, with Kirsten Dunst as his love interest Mary Jane. The actors reunited (along with James Franco and director Sam Raimi) for the sequels Spider-Man 2 (2004) and Spider-Man 3 (2007). Maguire also starred as jockey Red Pollard in the 2003 film Seabiscuit.

Extra credit: Maguire finished 291st out of 6538 players in the 2007 World Series of Poker in Las Vegas. The finish earned him prize money of $39,445.