Charlie Sheen

With Martin Sheen for a father, it's not surprising that Charlie Sheen became a film and TV star. Yet this bad-boy actor is even more famous for his off-screen antics. After making a splash in a succession of '80s blockbusters (Wall Street, Young Guns, Platoon), Sheen began drinking, drugging and hiring high-priced hookers from Hollywood madam Heidi Fleiss. In the '90s he landed in court multiple times for drug possession and assault, and professionally, was relegated to parts in B-movies (The Chase, Money Talks). But Sheen made a professional and personal comeback in the new millennium by joining the cast of Spin City and marrying bombshell Denise Richards. While his TV success continued with the sitcom Two and a Half Men, which snagged Sheen his first Emmy nod, his real life faltered when Richards left him in 2005 while pregnant with their second child and subsequently accused him of serial infidelity and physical abuse.