2. George Clooney
People mag's two-time Sexiest Man Alive already has an Oscar for acting, for 2005's Syriana. And he came damn close to catching Academy gold for directing Good Night, and Good Luck in the same year. Clooney debuted behind the camera with 2002's Confessions of a Dangerous Mind, suffered a setback with 2008's Leatherheads, and then came back swinging as director and actor in the 2011 political drama, The Ides of March.