(1960-)

Who Is Sean Penn?

Actor and filmmaker Sean Penn made 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. He has won several honors as an actor and filmmaker, including two Academy Awards for best actor. In early 2016, Penn found himself embroiled in controversy following his Rolling Stone interview with fugitive drug lord Joaquin “El Chapo” Guzman.

Early Life

Sean Justin Penn was born on August 17, 1960, in Santa Monica, California. His father, Leo, was an actor and director. His mother, Eileen Ryan, was an actress. 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).

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.

Acting and Directing Career

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.

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. 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. 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.

‘El Chapo’ Meeting

In an 11,000-word article published on Rolling Stone‘s website on January 9, 2016, Penn revealed that he had met with Mexican drug kingpin Joaquín “El Chapo” Guzmán at an undisclosed location in October 2015. Guzmán, who had orchestrated a daring escape from a high-security prison three months earlier, was looking to have a movie made about his life, and had agreed to an interview through Penn’s contact with Mexican actress Kate del Castillo.

In the article, Penn marveled at the security measures taken by El Chapo’s men, including their transportation aboard a plane with a device to jam radar signals, as well as the healthy, relaxed condition of one of the world’s most wanted fugitives. He noted, “I take no pride in keeping secrets that may be perceived as protecting criminals, nor do I have any gloating arrogance at posing for selfies with unknowing security men . . .This will be the first interview El Chapo had ever granted outside an interrogation room, leaving me no precedent by which to measure the hazards.”

The article was published one day after Guzmán’s recapture in Los Mochis, Mexico. Mexican authorities said they were able to zero in on the drug lord’s location through his cell phone and electronic exchanges, although it was unclear whether any of those exchanges were with Penn. It was also unclear whether the actor was facing legal problems for his involvement in the situation.

‘Bob Honey’ Audiobook and Novel

In 2016, Penn narrated an audiobook titled Bob Honey Who Just Do Stuff. Allegedly written by a man named Pappy Pariah, Bob Honey tells the story of a middle-aged man who worries about the state of his country while working for the government as a hitman.

Penn followed in 2018 by fleshing the work out in novel form. Along with its puzzling vocabulary, the book came under fire for a diatribe that suggested killing the president, as well as a poetic epilogue that criticized aspects of the #MeToo movement. The New York Times referred to it as a “a riddle wrapped in an enigma and cloaked in crazy.”

The book’s publisher, Atria, followed with full-page ads in The New York Times and The Washington Post, in which snippets of critical quotes are countered with a teaser for positive reviews at the company website and a challenge to “read it and decide for yourself.” Atria also issued a press release that questioned whether Penn was being given a fair chance to “expand his artistic profile” amid the “growing culture of divisiveness” in the country.

Personal Life

Seven years after his divorce from Madonna, Penn and House of Cards star Robin Wright wed in 1996. The couple has two children. The couple divorced in 2010 in a non-amicable split. In early 2014, reports surfaced that Penn was dating a fellow Oscar winner, actress Charlize Theron. They quietly got engaged that December, but by the following June, it was revealed that the couple had ended their relationship.

In August 2020, Penn tied the knot with Leila George, his girlfriend of four years.

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QUICK FACTS

• Name: Sean Penn
• Birth Year: 1960
• Birth date: August 17, 1960
• Birth State: California
• Birth City: Santa Monica
• Birth Country: United States
• Gender: Male
• Best Known For: Academy Award-winning actor Sean Penn is known for his starring roles in films such as ‘Fast Times at Ridgemont High,’ ‘Mystic River’ and ‘Milk.’
• Industries
• Drama
• Action
• Comedy
• Astrological Sign: Leo

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CITATION INFORMATION

• Article Title: Sean Penn Biography
• Author: Biography.com Editors
• Website Name: The Biography.com website
• Url: https://www.biography.com/actors/sean-penn
• Access Date:
• Publisher: A&E; Television Networks
• Last Updated: March 30, 2021
• Original Published Date: April 2, 2014