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Two actually: He won Best Actor for Jimmy Markum in Mystic River (2003) and Milk (2008).

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Penn has been nominated five times for Best Actor, winning twice: 1995 Dead Man Walking 1999 Sweet and Lowdown 2001 I Am Sam 2003 Mystic River (won) 2008 Milk (won)

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Q: How many Oscar nominations does Sean Penn have?
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