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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).
Penn launched his film career with the action-drama Taps (1981), where he played a military high school cadet.
Lee was a former drug dealer by trade, convicted of espionage for the Soviet Union and originally sentenced to life in prison, but was paroled in 1998.
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.
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 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.
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.
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).
Penn has been outspoken in supporting numerous political and social causes.