Although he was working steadily in B-movies and bad TV series by his midtwenties, this magnetic actor didn't become a sex symbol and megastar until he landed the plum role of a rogue doctor on ER in 1994. Fame, film roles and the tabloids followed, yet after a string of wooden performances in high-priced flops, including The Peacemaker and Batman & Robin, it looked like his career might go the way of David Caruso's. But in the early '00s, Clooney bounced back by appearing in a wide array of roles: a dashing criminal in Ocean's Eleven, a goofy fugitive in O Brother, Where Art Thou?, and a dead serious CIA operative in 2005's Syriana, which earned him both a Golden Globe and an Oscar as Best Supporting Actor. That same year, Clooney also tried his hand behind the camera, netting Golden Globe and Academy Award nods as a director and screenwriter for Good Night, and Good Luck. Off screen, other than a brief marriage to Talia Balsam when he was young, this hunk is a notorious bachelor who has been linked with a long list of lovely ladies.