Sean Penn

Season 5, Episode 503

Original Airdate: February 28, 1999

Sean Penn is the second of three sons born to actress Eileen Ryan and director Leo Penn. Older brother Michael is a respected musician (having recently done music on films such as Boogie Nights and Magnolia) and younger brother Christopher is also an actor (Footloose, Reservoir Dogs, Short Cuts). His neighbors growing up were Martin Sheen's kids Charlie Sheen and Emilio Estevez, whom Penn was good friends with throughout his youth.

Penn was born and bred in the showbiz milieu, is acknowledged as one of the most talented actors of his generation, and has nothing but contempt for the Hollywood machine. He originally wanted to enter the law profession, but changed his mind and joined the Los Angeles Repertory Theater after high school. It wasn't long before he had moved on from the stage to bit-part television appearances.

Penn moved to New York in 1980, and promptly landed both his debut feature-film role, in Taps (1981), and an off-Broadway appearance, in a production of Heartland. Among a host of other young actors, Penn stood out as the lovable stoner Jeff Spicoli in the seminal teen flick Fast Times at Ridgemont High. Penn went from being a relative unknown to a rising star.

He followed up with Bad Boys (1983) and Racing With the Moon (1984) and drew critical interest in his talent. Three years later, Penn played a coke addict who sells government secrets to Soviet agents in John Schlesinger's fact-based drama The Falcon and the Snowman.

Already a star at age 24, Penn's acting career was sidelined by his personal life in 1985, when a visit to the set of Madonna's Material Girl video shoot turned into a trip down the aisle later that year. Their tumultuous three-year marriage ended in divorce, with rumors about Penn's temper rampant, especially after well-publicized incidents lashing out at the paprazzi.

Though Penn delivered rock-solid performances in Casualties of War and State of Grace (1990), the fallout from his divorce left him soured on Hollywood. However, State of Grace introduced him to his second wife, Robin Wright (The Princess Bride, Forrest Gump), with whom he has two children.

In 1991, he wrote, produced and directed his first film, The Indian Runner. Though only in his early 30s, Penn announced that he was retiring from acting to pursue a full-time career as a director. However, it was much harder to pay the bills as an independent-minded director in Hollywood than as a well-known actor, and he returned to the screen for a knockout performance as Al Pacino's sleazy lawyer confidante in 1993's Carlito's Way.

1995 was a landmark year for Penn, with success in both directing and acting. His second film as writer-director-producer yielded The Crossing Guard, which reunited Jack Nicholson and Angelica Huston on screen. That same year, Penn returned to acting again with a moving and humanistic (and Oscar-nominated) portrayal of a convicted rapist and murderer on death row in Dead Man Walking.

In 1997, Penn produced and starred in She's So Lovely, with wife Robin and John Travolta. The film was written by John Cassavetes and directed by son Nick after his death. Penn won the Cannes Film Festival's Best Actor award for his role. He played opposite Michael Douglas in the haunting thriller The Game, and also starred in Oliver Stone's U-Turn. In 1998, Penn appeared in Terrence Malick's The Thin Red Line, and in a film adaptation of playwright David Rabe's Hurlyburly.

1999 brought another Oscar-nomination for his role as a drunken jazz guitarist in Woody Allen's comedy Sweet and Lowdown. Most recently, Penn directed his wife and Jack Nicholson in The Pledge (2001) and he has a role in the upcoming film, I am Sam, co-starring Michelle Pfeiffer. He plays a mentally-challenged man fighting for custody of his child.