RDJ is the definition of a Hollywood comeback kid. After portraying a conflicted teen in 1987's Less Than Zero, many of the problems he acted out in the film found their way into his personal life in the late '90s. He was in movies again by 2003, but 2008 was the year Downey really got his swagger back. Iron Man and Tropic Thunder were both summer blockbusters, with his performance in the latter earning him an Oscar nomination for Best Supporting Actor.