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Clint Eastwood (May 31st, 1930), the American actor, director and producer has won 4 Oscars:-1992: Oscar to the Best Director and Oscar to the Best Picture for 'Unforgiven'.-1992: Oscar to the Best Director and Oscar to the Best Picture for 'Million Dollar Baby'.
Rating Newest Oldest. 1  Clint Eastwood has been nominated for 11 Oscars. He as won 4 oscars (including Best Movie, Best Director) Adventure Â· 3 years ago. 2  Clint Eastwood has FOUR Oscars. Two for producing and two for directing. 3  I know Unforgiven won a couple of Oscars and I think he got best director. He's popular among his peers but I've never found him particularly original. Unforgiven was good, though.