He has won two Academy Awards, for his roles in the mystery drama Mystic River (2003) and the biopic Milk (2008).
Penn began his acting career in television, with a brief appearance in episode 112 of Little House on the Prairie on 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) and Bad Boys (1983).
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.