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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).
The film was a critical and commercial failure, named by a 2010 Forbes article as the biggest flop in the last five years.
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).
Bush administration, his contact with the Presidents of Cuba and Venezuela, and his humanitarian work in the aftermath of Hurricane Katrina in 2005 and the 2010 Haiti earthquake.
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.
In 2015, Penn starred in The Gunman, a French-American action thriller based on the novel The Prone Gunman, by Jean-Patrick Manchette.
Jasmine Trinca, Idris Elba, Ray Winstone, Mark Rylance and fellow Oscar-winner Javier Bardem appear in supporting roles.
Madonna reportedly filed an assault complaint that she was beaten in her Malibu, California, home by her estranged husband, but in January 1989, the Associated Press reported that she had "dropped assault charges."Penn and Wright separated in 1995, during which time he developed a relationship with Jewel, after he spotted her performing on Late Night with Conan O'Brien.