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5. Oscar History

Penn’s 1995 film, Dead Man Walking, earned him his first Oscar nomination. He was nominated again in 2000 for Woody Allen’s Sweet and Lowdown as well as in 2002 for I Am Sam. Penn finally won the Oscar in 2004 for Best Actor in a Leading Role for Mystic River and again in 2009 for Best Performance of a Leading Actor as gay-rights icon Harvey Milk.

sean penn
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