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He is known for his anti-hero acting roles in violent action and western films. Following his six-year run on the television series Rawhide (1959–65), he starred as the Man With No Name in Sergio Leone's Dollars Trilogy of Spaghetti Westerns in the 1960s, and as Inspector Harry Callahan in the Dirty Harry films in the 1970s and 1980s. These roles have made him an enduring cultural icon of masculinity.He is also notable for his comedic efforts in Every Which Way But Loose (1978) and its sequel Any Which Way You Can (1980), his two highest-grossing films after adjustment for inflation. For his work in the films Unforgiven (1992) and Million Dollar Baby (2004), He won Academy Awards for Best Director and for producer of the Best Picture, and received nominations for Best Actor. These films in particular, as well as others including Paint Your Wagon (1969), Play Misty for Me (1971), High Plains Drifter (1973), The Outlaw Josey Wales (1976), Escape from Alcatraz (1979), Pale Rider (1985), In the Line of Fire (1993), and Gran Torino (2008), have all received great critical acclaim and commercial success. He has directed most of his star vehicles as well as films he has not acted in, such as Mystic River (2003) and Letters from Iwo Jima (2006), for which he received Academy Award nominations.