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He was nominated again for his comedic performance as an egotistical jazz guitarist in the film Sweet and Lowdown (1999).He received his third nomination after portraying a mentally handicapped father in I am Sam (2001).Penn finally won for his role in the Boston crime-drama Mystic River (2003).In 2004, Penn played Samuel Bicke, a character based on Samuel Byck, who in 1974 attempted and failed to assassinate President Richard Nixon, in The Assassination of Richard Nixon (2004).The film also earned Penn his fifth nomination and second win for the Academy Award for Best Actor. Wilson in Fair Game (2010), a film adaptation of Valerie Plame's 2007 memoir.
Penn appeared in a 1974 episode of the Little House on the Prairie television series as an extra when his father, Leo, directed some of the episodes.Penn received another two Oscar nominations for Woody Allen's comedy-drama Sweet and Lowdown (1999) and the drama I Am Sam (2001), before winning his first Academy Award for Best Actor in 2003 for Mystic River and a second one in 2008 for Milk.He has also won a Best Actor Award of the Cannes Film Festival for the Nick Cassavetes-directed She's So Lovely (1997), and two Best Actor Awards at the Venice Film Festival for the indie film Hurlyburly (1998) and the drama 21 Grams (2003).Penn plays Jim Terrier, a sniper on a mercenary assassination team who kills the minister of mines of the Congo.Penn made his directorial debut with The Indian Runner (1991), a crime drama film based on Bruce Springsteen's song "Highway Patrolman", from the album Nebraska (1982).
The film was a critical and commercial failure, named by a 2010 Forbes article as the biggest flop in the last five years.