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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).
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).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.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 has since directed three more films, all well received by critics: the indie thriller The Crossing Guard (1995), the mystery film The Pledge (2001), and the biographical drama survival film Into the Wild (2007). The two starred in the panned and much-derided Shanghai Surprise (1986), directed by Jim Goddard, and Madonna dedicated her third studio album True Blue (1986) to Penn, referring to him in the liner notes as "the coolest guy in the universe".The relationship was marred by violent outbursts against the press, including one incident when Penn was arrested for assaulting a photographer on a film set; Penn was sentenced to 60 days in jail in mid-1987, of which he served 33 days.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.
is an American actor, filmmaker, and political activist.
Penn made his directorial debut with The Indian Runner (1991), a crime drama film based on Bruce Springsteen's song "Highway Patrolman", from the album Nebraska (1982).
He also directed music videos, such as Shania Twain's "Dance with the One That Brought You" (1993), Lyle Lovett's "North Dakota" (1993), and Peter Gabriel's "The Barry Williams Show" (2002).
Bush administration, his contact with the Presidents of Cuba and Venezuela, and his humanitarian work in the aftermath of Hurricane Katrina (2005) and the 2010 Haiti earthquake.