George Clooney — 8 Films, 2 Oscar Noms

Clooney directed Confessions of a Dangerous Mind (2002), Good Night and Good Luck (6 Oscar nominations, including Best Director for Clooney), The Ides of March, and The Boys in the Boat. He uses directing as artistic counterbalance to his $1 billion tequila-selling persona — choosing politically charged, adult-oriented dramas that studios increasingly won't fund. Good Night and Good Luck was made for $7 million and earned $54 million — a 7.7x return. His directorial work is never flashy, but it's consistently intelligent and commercially viable. The tequila funds the art films.