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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.

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.

The film also earned Penn his fifth nomination and second win for the Academy Award for Best Actor. Wilson in Fair Game (2010), a film adaptation of Valerie Plame's 2007 memoir.

He co-starred in the drama The Tree of Life (2011), which won the Palme d'Or at the 2011 Cannes Film Festival.

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.

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).

In 2004, Penn played Samuel Bicke, a character based on Samuel Byck, who in 1974 attempted and failed to assassinate President Richard Nixon, in The Assassination of Richard Nixon (2004).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).The film was a critical and commercial failure, named by a 2010 Forbes article as the biggest flop in the last five years.In November 2008, Penn earned positive reviews for his portrayal of real-life gay-rights icon and politician Harvey Milk in the biopic Milk (2008), and was nominated for best actor for the 2008 Independent Spirit Awards.

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