George Clooney — 8 Films, 2 Oscar Noms

His third film, Good Night and Good Luck (2005), received 6 Oscar nominations, including Best Picture, and was made for $7 million while earning $54 million globally (a 7.7x return). Clooney chooses politically charged, adult-oriented dramas that studios increasingly won't fund, directing actors including John Krasinski and Lily Rabe. His $1 billion tequila-selling persona funds these art films, but he uses directing as an artistic counterbalance rather than a full transformation. While not flashy, his work is consistently intelligent and commercially viable.