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On December 13–16, 2002, he visited Iraq to protest the Bush Administration's apparent plans for a military strike on Iraq. Acting as a journalist on an assignment for the San Francisco Chronicle, he attended a Friday prayer at Tehran University.

On January 7, 2006, Penn was a special guest at the Progressive Democrats of America, where he was joined by author and media critic Norman Solomon, Democratic congressional candidate Charles Brown, and activist Cindy Sheehan.

Penn began his acting career in television with a brief appearance in episode 112 of Little House on the Prairie (December 4, 1974), directed by his father Leo Penn.

Following his film debut in the drama Taps (1981) and a diverse range of film roles in the 1980s, including Fast Times at Ridgemont High (1982), Penn garnered critical attention for his roles in the crime dramas At Close Range (1986), State of Grace (1990), and Carlito's Way (1993).

He became known as a prominent leading actor with the drama Dead Man Walking (1995), for which he earned his first Academy Award nomination and the Best Actor Award at the Berlin Film Festival.

His fourth feature film, the biographical drama survival movie Into the Wild (2007), garnered critical acclaim and two Academy Award nominations.

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 launched his film career with the action-drama Taps (1981), where he played a military high school cadet.

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).

He was nominated again for his comedic performance as an egotistical jazz guitarist in the film Sweet and Lowdown (1999).

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