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Sean Penn

It took Penn almost 30 years in the biz before the Academy gave him an Oscar, for his turn as the distraught father of a murdered girl who takes the law into his own hands, in Mystic River. His second winner was for his depiction of San Francisco’s first openly gay mayor, in Milk. Next up for Penn is a remake of The Three Stooges. Three-time winner? Maybe not yet.

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