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).
He has also won a Best Actor Award of the Cannes Film Festival for the Nick Cassavetes-directed She's So Lovely (1997), and two Best Actor Awards at the Venice Film Festival for the indie film Hurlyburly (1998) and the drama 21 Grams (2003).
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).
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.
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).that Robin's "very disapproving of what’s been going on, and his friends have warned him against the relationship. In fact, he has reportedly already moved her into his mansion!"Sean is already head over heels in love with Leila, but his friends think he’s totally crazy to move in with her so fast," added the insider.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.is an American actor, filmmaker, and political activist.