Michael Clayton Oscar History: Three nominations, one win (for Syriana in 2006). 2008 Scorecard: He won a National Board of Review award and was nominated for Golden Globe, Screen Actors Guild and Critics' Choice awards. Before He Hit Oscar: The Kentucky native tried out for a spot with the Cincinnati Reds baseball team. A Different Direction: "My hope is that as time goes on and people want to see less and less of me onscreen," Clooney, 46, told Time, "I'll be able to direct."