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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.He co-starred in the drama The Tree of Life (2011), which won the Palme d'Or at the 2011 Cannes Film Festival.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 at 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).He also directed music videos, such as Shania Twain's "Dance with the One That Brought You" (1993), Lyle Lovett's "North Dakota" (1993), and Peter Gabriel's "The Barry Williams Show" (2002).

The Academy Awards first recognized his work in nominating him for playing a racist murderer on death row in the drama film Dead Man Walking (1995).

The relationship was marred by violent outbursts against the press, including one incident when Penn was arrested for assaulting a photographer on a film set; Penn was sentenced to 60 days in jail in mid-1987, of which he served 33 days.

but later withdrew the papers, only to file them again in January 1989.

The same year, he was invited to join the Academy of Motion Picture Arts and Sciences.

Next, Penn portrayed governor Willie Stark (based on Huey Long) in an adaptation of Robert Penn Warren's classic 1946 American novel All the King's Men (2006).

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