Sean Justin Penn (born August 17, 1960) is an American actor, screenwriter and film director, also known for his political and social activism. He is a two-time Academy Award winner for his roles in Mystic River (2003) and Milk (2008), as well as the recipient of a Golden Globe Award for the former and a Screen Actors Guild Award for the latter.

He served 32 days in jail in 1987 for hitting an extra.
He and Robin Wright lived together from 1991 until their marriage in 1996. They had two children before their marriage.
They lost their home in the Malibu fire in November 1993.
Appeared with his brother Chris Penn in At Close Range (1986), in which their actress mother, Eileen Ryan, played their grandmother.
Listed as one of twelve “Promising New Actors of 1984″ in John Willis’ Screen World, Vol. 36.
Ranked #76 in Empire (UK) magazine’s “The Top 100 Movie Stars of All Time” list. [October 1997]
Son of Leo Penn and Eileen Ryan.
Middle brother of musician Michael Penn and Chris Penn.
Moved to Marin County (North of San Francisco) to avoid raising his children in Hollywood.
Daughter, with Robin Wright, Dylan Penn (b. 13 April 1991).
Son, with Robin Wright, Hopper Penn (b. 6 August 1993).
His son is named after two family friends, Dennis Hopper and Jack Nicholson.
Brother-in-law of Aimee Mann.
Quit smoking for a while on his 40th birthday for health reasons. Prior to that, he was known as one of Hollywood’s heaviest smokers, smoking at least four packs of cigarettes a day.
On September 11, 2004, he received the John Steinbeck award at the Palace of Fine Arts in San Francisco. The award is given out by the San Francisco Chronicle and benefits San Jose State University. The evening included film clips and discussion with Peter Coyote. The biggest surprise of the night was that Bruce Springsteen (a longtime friend of Sean’s and the first recipient of the award) presented it to him.
His father was of mostly Russian and Lithuanian descent, but paternal grandfather, whose original surname was Piñon, was of Sephardic Jewish heritage. His mother was of Irish and Italian heritage. His paternal grandparents ran a Jewish deli for some time in New York.
In October 2002, he bought a $56,000 ad in the Washington Post to publish an open letter to President George W. Bush asking him to slow down the march of war towards Iraq. He wrote it as a father of two children and as a son of a WW II veteran.
His father, Leo Penn, had been blacklisted in the 1950s for his political beliefs.
He and his family moved out of Hollywood to Marin County, north of San Francisco because he was “tired of a lot of aspects of Los Angeles, the main one being raising the kids in a company town”.
His car, a limited-edition 1987 Buick Grand National, was stolen in Berkeley months after his return from Iraq. Among the lost contents were 2 guns.
He and director Clint Eastwood discussed the possibility of Sean starring in Blood Work (2002). Though it didn’t work out, they got the opportunity to work together later in Mystic River (2003).
Andy Warhol was a guest during his August 16, 1985 marriage to Madonna.
A popular indie-band in The Netherlands is called “Seanpenn”.
Briefly engaged to actress-photographer Pamela Springsteen, sister of Bruce Springsteen. The two were both in Fast Times at Ridgemont High (1982).
Credits Malcolm McDowell as the best actor with whom he’s worked.
As of 2005, the only actor to ever receive a Best Actor nomination for a Woody Allen film, besides Allen himself.
His performance as “Jeff Spicoli” in Fast Times at Ridgemont High (1982) is ranked #9 on Premiere Magazine’s 100 Greatest Movie Characters of All Time.
Refuses to talk about his ex-wife Madonna in interviews. On her 1989 “Like A Prayer” album, she wrote a song about their failed marriage called “Till Death Do Us Part”.
Was in the same acting class as Michelle Pfeiffer at the end of the 70s or early 80s.
Good friends with Metallica drummer Lars Ulrich.
Wife Robin Wright filed papers for divorce after 11 years of marriage on December 21, 2007, citing irreconcilable differences. The couple is seeking joint custody of their two teenage children. In April 2008 they withdrew the petition.
Is an avid surfer.
2008′s Jury president of Cannes Film Festival.
He toured Caracas, Venezuela, in August 2007 with President Hugo Chávez,.
Former brother-in-law of Christopher Ciccone, Martin Ciccone, Paula Ciccone, Anthony Ciccone, Melanie Ciccone, Mario Ciccone, and Jennifer Ciccone.
Former son-in-law of Silvio Ciccone.
Milo Ventimiglia listed him as his favorite actor.
He and ex-wife Madonna’s birthdays are a day apart.
He is the 9th person to win 2 Academy Awards for Best Actor.
Is very good friends with Robert De Niro. The two share the same birthday and would often throw a joint birthday party together.
In October 2008, he traveled to Cuba where he met with and interviewed President Raúl Castro.
Filed for divorce from Robin Wright, a year after they reconciled after she had filed for divorce in late 2007. [April 2009]
Requested to withdraw the papers he filed for legal separation from Robin Wright. [May 2009]
Lost out to Christopher Atkins for the role of Richard in The Blue Lagoon (1980) on the final day of auditions.
His publicist is Mara Buxbaum.
Robin Wright once again filed for divorce. She had previously stated in More magazine that, although they withdrew their divorce papers in early 2009, they are no longer together. [August 2009]
Born at 3:17 PM (PDT).
Flew to Haiti on January 21 2010 to help the relief effort after the earthquake.
Penn’s At Close Range (1986) director James Foley served as best man at Penn and Madonna’s wedding (1985).
In June 1987 Penn was sentenced to sixty days for probation violations including reckless driving and assault. The sentence was reduced to thirty-three days “in anticipation of good behavior.” Penn served five days, was released to film a movie, and then served out the remainder of his sentence in private jail facilities for which he paid an extra eighty dollars per day.
Was ordered to complete 300 hours of community service and 36 hours of anger management therapy after being charged with misdemeanor vandalism. Penn reportedly kicked a paparazzi in the leg in October 2009 and was initially charged with battery and vandalism. [May 2010]
Is the subject of the song ‘Sean Penn Blues’ by Lloyd Cole & The Commotions.