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Penn made his feature film directorial debut with The Indian Runner (1991), followed by the drama film The Crossing Guard (1995) and the mystery film The Pledge (2001).

Penn directed one of the 11 segments of 11'09"01 September 11 (2002), a compilation film made in response to the September 11 attacks.

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.

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).

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.He co-starred in the drama The Tree of Life (2011), which won the Palme d'Or at the 2011 Cannes Film Festival.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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Penn later hired Lee as his personal assistant, partly because he wanted to reward Lee for allowing him to play Lee in the film; Penn was also a firm believer in rehabilitation and thought Lee should be successfully reintegrated into society, since he was a free man again.