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Answer:
SEANPENN
Possible Questions:
He played himself in "Being John Malkovich"
"Mystic River" co-star, 2003
Oscar winner for "Mystic River" and "Milk"
Half of a 1980s power couple
Brad Pitt's costar in "The Tree of Life"
Best Actor of 2003
Aimee Mann's brother-in-law
2008 Harvey Milk portrayer
"Mystic River" costar