Clint Eastwood Clint Eastwood is Hollywood legend. He got his big break in 1959 when he starred as Rowdy Yates in the long-running television series Rawhide. He spent most of the 60s playing cowboys; in the 70s he trended toward tough-talking cops like Harry Callahan in Dirty Harry, and in the '80s he somehow landed a whole lot of military roles. Post-'80s highlight: Four Oscar awards for Million Dollar Baby, a film he directed and starred in, including Best Picture, Best Director. Post-'80s lowlight: Not too much has gone wrong for Clint over the years, but 1997s Midnight in the Garden of Good and Evil was not a great film. Where are they now? Eastwood did two films about World War II -- Flags of Our Fathers and Letters From Iwo Jima, two well-received 2008 films -- The Changeling" with Angelina Jolie and "Gran Torino" -- and the South African sports drama "Invictus."
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