Denzel Washington — 1990

Age: 35

Winner: Actor in a Supporting Role, Glory #Fact: In addition to his Glory win, Denzel was nominated for Actor in a Supporting Role in Cry Freedom in 1988. He took home an Oscar in 2002 for Actor in a Leading Role in Training Day and has been nominated a total of eight times, including two nominations this year — Actor in a Leading Role and Best Picture for Fences.