Born in Santa Monica, CA; son of actress Eileen Ryan (b. 1928); brother of actor Chris Penn (1965-2006). Intense, gifted performer whose accomplishments as a movie player were often overshadowed by his reputation as a spoiled brat and his penchant for violent outbursts offscreen. The son of TV and film distributor Leo Penn and actress Eileen Ryan, he skipped college and joined the Group Repertory Theatre of Los Angeles as an apprentice directly after graduating from Santa Monica High School. He made his professional debut in 1979 as a guest performer in an episode of the TV series "Barnaby Jones" and his first film appearance in 1981, in TAPS. From the start he struck audiences as different, an actor with a natural gift and estimable range whose intense personality shone through even in mediocre vehicles. But Penn's reputation as Hollywood's bad boy continued to plague his career, especially after his 1985 marriage to flamboyant singer-actress Madonna. The constant press attention surrounding the star marriage led him to fits of temper and public brawling. In 1987 he served a six-month jail term for assault. After the stormy on-again-off-again marriage ended in divorce in 1989, Penn married actress Robin Wright and seemed to have gained peace of mind. In 1991, while prematurely announcing his retirement from screen acting, he made his debut as a film director-writer with THE INDIAN RUNNER, a raw and rambling drama about two brothers of conflicting outlooks and temperaments. In the 90s Penn established himself as one of Hollywood's most talented and charismatic on-screen personalities, turning in outstanding performances in such films as DEAD MAN WALKING (1995), opposite Best Actress winner Susan Sarandon, and Woody Allen's SWEET AND LOW DOWN (1999), both of which earned him Best Actor nominations. He also starred in THE THIN RED LINE (1998), I AM SAM (2001, another Oscar® nomination), IT'S ALL ABOUT LOVE, 21 GRAMS and MYSTIC RIVER (all 2003), THE ASSASSINATION OF RICHARD NIXON (2004), THE INTERPRETER (2005), ALL THE KING'S MEN (2006, CROSSING OVER and MILK (both 2008), and TREE OF LIFE (scheduled for release in 2009). As producer and director, he has helmed THE CROSSING GUARD (1995, also writer), THE PLEDGE (2001), and INTO THE WILD (2007, also screenplay). Penn was married to actress/pop singer Madonna (b. 1958) from 1985 to 1989. He and his second wife, actress Robin Wright Penn (b. 1966), married in 1996. They have 2 children. Visit the Internet Movie Database for a full listing of Penn's acting, producing and directing credits.  Nominated for Best Performance by an Actor in a Leading Role 1995: DEAD MAN WALKING  Nominated for Best Performance by an Actor in a Leading Role 1999: SWEET AND LOWDOWN  Nominated for Best Performance by an Actor in a Leading Role 2001: I AM SAM  Best Actor in a Leading Role 2003: MYSTIC RIVER 4 nominations, 1 Award