His early career was built on spaghetti westerns, especially the Man With No Name trilogy ("Fistful of Dollars" (1964), "For a Few Dollars More" (1965), and "The Good, the Bad, and the Ugly" (1966)). His career then exploded in the '70s with the Dirty Harry movies, and the role of loose cannon enforcer has been mimicked in nearly every cop movie since. He then closed the '70s with "Escape from Alcatraz" (1979). His career declined in the late '80s, but he bounced back in '92 with "Unforgiven," winning the Oscar for Best Director and the movie itself capturing Best Picture. After that, his directing cap brought him to the Oscars with "Mystic River" (2003), "Million Dollar Baby" (2004), and "Letters from Iwo Jima" (2006), which all earned nominations for Best Picture (you already know "Million Dollar Baby" won). Eastwood then became the oldest leading man to reach No. 1 at the box office with the movie "Gran Torino" (2008).
Source: Warner Bros./AP