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.His fourth feature film, the biographical drama survival movie Into the Wild (2007), garnered critical acclaim and two Academy Award nominations.Penn finally won for his role in the Boston crime-drama Mystic River (2003).
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 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).
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).to actor and director Leo Penn, and actress Eileen Ryan (née Annucci). His younger brother, actor Chris Penn, died in 2006.His paternal grandparents were Ashkenazi Jewish emigrants from Lithuania and Russia, 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."There’s a foundation of twenty years that the two of us have shared with each other in all these different ways that is really the foundation of something that has brought a lot of beautiful things into my life," Theron told Esquire."We get so stuck in wanting to predict the future that we forget the moment that we’re in.In January 2016, Penn published an interview (conducted in October 2015) with Mexican drug lord Joaquín "El Chapo" Guzmán in Rolling Stone.