Sexiest Man Alive 2009: By the time Depp, 46, landed his second PEOPLE's Sexiest Man cover in 2009 (his first was in 2003), he was famous for his zany portrayal of Captain Jack Sparrow in the Pirates of the Caribbean movies, his non-Hollywood lifestyle (he and his family lived mostly in France) and his chiseled cheekbones. Now: Depp just turned 50, which he's fine with, if only for the clothing options. "As you get older you can . . . wear anything you want; old people dress cool," jokes the actor, who has been stepping out with actress Amber Heard since his 2012 split from Vanessa Paradis.