Sean Penn Biography

Academy Award-winning actor Sean Penn starred in 'Fast Times at Ridgemont High,' 'Mystic River' and 'Milk,' married Madonna and directed Jack Nicholson in two films.

Synopsis

Born in California on August 17, 1960, Sean Penn began his acting career on Broadway before making his film debut in 1981's Taps. His breakout role came in 1982, when he played Jeff Spicoli in Fast Times at Ridgemont High. Later acting work included Dead Man Walking (1995) and She's So Lovely (1997), and writing, producing and directing The Crossing Guard (1995), among other projects. Penn's more recent acting credits include Up in the Villa, The Weight of Water, All the King's Men, I Am Sam, Milk and Tree of Life; directing credits include The Pledge and Into the Wild. He has won several honors as a thespian and filmmaker, including two Academy Awards for best actor.

Young Hollywood

Actor Sean Justin Penn was born on August 17, 1960, in Santa Monica, California. His father, Leo Penn, was an actor and director. His mother, Eileen Ryan, was an actress. Sean Penn grew up in Los Angeles, and attended Santa Monica High School along with fellow students and future actors Emilio Estevez, Charlie Sheen and Rob Lowe.

An  interest in filmmaking, specifically directing, led to Penn's passion for acting, which included several early TV parts. He moved to New York City at the age of 19 and soon landed a part in a Broadway play, Heartland. In 1981, he made his film debut alongside budding star Tom Cruise and Academy Award winner Timothy Hutton in the military school drama Taps.

Penn's breakthrough role came a year later, when he played the perpetually stoned surfer Jeff Spicoli in the high school comedy Fast Times at Ridgemont High (1982) opposite Jennifer Jason Leigh and Judge Reinhold. Penn then garnered acclaim for his first starring role in 1983's Bad Boys and for the drama The Falcon and the Snowman (1985).

Bad Boy Image

In 1985, Penn gained a whole new measure of fame when he married pop icon Madonna. Their tumultuous four-year marriage produced one dismal movie, 1986's Shanghai Surprise, and a barrage of tabloid headlines. Penn's "bad boy" image only increased with his continued hostility toward the aggressive paparazzi—he served 34 days in prison in 1987 for punching an extra who tried to take his picture. Penn and Madonna divorced in 1989.

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Array of Films

In 1991, two years after earning rave reviews for his performance in Casualties of War (1989), Penn directed his first film. The feature The Indian Runner opened to a limited release and ultimately made a bit less than $200,000 at the box office. Critics gave the film mild praise.

Though he previously claimed he quit acting, Penn returned to the front of the camera in 1993, playing a coke-addled criminal lawyer in Brian De Palma's Carlito's Way, co-starring Al Pacino. His performance earned him a Golden Globe nomination for best supporting actor.

Then in 1995, he starred as a death row inmate searching for salvation in the film Dead Man Walking, based on the true story by Helen Prejean. The film earned Penn Academy Award and Golden Globe nominations, as well as an Independent Spirit Award. The film also did well with audiences, grossing more than $80 million worldwide.

That same year, he wrote, produced and directed The Crossing Guard, a dark drama starring his boyhood idol, Jack Nicholson. The film received positive reviews from critics, as well as a Golden Globe nomination for Anjelica Huston.

Recognition for 'Mystic River'

Penn next starred as a lovesick, jealous husband in Nick Cassavetes's She's So Lovely (1997), co-starring John Travolta and Penn's real-life second wife, Robin Wright Penn. Although Penn (who also served as executive producer) won the Best Actor Award at the Cannes Film Festival, She's So Lovely did not attract a wide audience.

Penn appeared in two other major films in 1997: the poorly received U-Turn, directed by Oliver Stone, and the hit action-thriller The Game, starring Michael Douglas. In Hurlyburly (1998), Penn reprised a role he played on the Los Angeles stage in 1988. That same year, he also starred in the critically acclaimed World War II drama The Thin Red Line, directed by Terrence Malick.

In 1999, the unpredictable Penn took Hollywood by surprise when he garnered a second Academy Award nomination for best actor, turning in another searing, darkly complex performance as the dissolute jazz guitarist at the center of Woody Allen's Sweet and Lowdown. In 2000, he starred in the romantic Up in the Villa with Kristen Scott Thomas, and in The Weight of Water. His third directorial feature, the thriller The Pledge, again starred Nicholson and Wright Penn. Then in 2002, Penn starred opposite Michelle Pfeiffer in I Am Sam, playing a mentally disabled man who fights to regain custody of his young daughter. He received his third Oscar nomination for the role.

The following year, he starred in Clint Eastwood's small town drama Mystic River, for which he earned an Academy Award for best actor. In 2006, Penn starred as Willie Stark, a fictional character based loosely on Louisiana governor Huey Long, in All the King's Men. He went on to direct the true-life story of a young man living in rural Alaska in Into the Wild (2007), starring Emile Hirsch. 

Second Oscar for 'Milk'

Stepping back in front of the cameras, Penn won his second Academy Award for best actor for his portrayal of the first openly gay politician, Harvey Milk, in the film Milk (2008). The film, directed by Gus Van Sant, received more than 40 award nominations and performed well at the box office. Penn later had a supporting role in the Malick film Tree of Life (2011). That same year, he starred in the independent drama This Must Be the Place, in which Penn played a former rock star who searched for a Nazi war criminal to avenge his father.

Penn tackled an infamous role in Gangster Squad (2013), a movie about the clash between law enforcement and organized crime in Los Angeles in the 1940s and 1950s. He portrayed the notorious crime boss Mickey Cohen and Ryan Gosling played a member of the police force who opposes him. The project had been scheduled for a fall 2012 release but was delayed because of the film's shootout scene in a movie theater, which evoked memories of the July 2012 shootings inside a Colorado movie theater. Warner Brothers, the studio behind Squad, subsequently made edits to the film.

Penn had a small supporting role in 2014's The Secret Life of Walter Mitty, starring Ben Stiller, and is featured in the 2015 action drama The Gunman. He also made headlines after the February 2015 Academy Awards telecast: Penn uttered an off-color joke about friend Alejandro Gonzales Iñárritu while announcing the director's Birdman win for best picture.

Personal Life

Penn and future House of Cards star Robin Wright had wed in 1996, going on to have two children. The couple divorced in 2010 in a non-amicable split. Then in early 2014, reports surfaced that Penn was dating a fellow Oscar winner, actress Charlize Theron. With their romance receiving ample media coverage, there's continued speculation over whether he and Theron will tie the knot.