His father, Leo Penn, had been blacklisted in the 1950s for his political beliefs.
Lost out to Christopher Atkins for the role of Richard in The Blue Lagoon (1980) on the final day of auditions.
Briefly engaged to actress-photographer Pamela Springsteen, sister of Bruce Springsteen. The two were both in Fast Times at Ridgemont High (1982).
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.
Listed as one of twelve "Promising New Actors of 1984" in John Willis' Screen World, Vol. 36.
Andy Warhol was a guest during his August 16, 1985 marriage to Madonna.
Appeared with his brother Chris Penn in At Close Range (1986), in which their actress mother, Eileen Ryan, played their grandmother.
Penn's At Close Range (1986) director James Foley served as best man at Penn and Madonna's wedding (1985).
He served 32 days in jail in 1987 for hitting an extra.
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.
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.
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".
He and Robin Wright lived together from 1991 until their marriage in 1996. They had two children before their marriage.
Daughter, with Robin Wright, Dylan Penn (b. 13 April 1991).
They lost their home in the Malibu fire in November 1993.
Son, with Robin Wright, Hopper Penn (b. 6 August 1993).
Ranked #76 in Empire (UK) magazine's "The Top 100 Movie Stars of All Time" list. [October 1997]
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).
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.
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.
As of 2005, the only actor to ever receive a Best Actor nomination for a Woody Allen film, besides Allen himself.
He toured Caracas, Venezuela, in August 2007 with President Hugo Chávez,.
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.
Filed for divorce from Robin Wright, a year after they reconciled after she had filed for divorce in late 2007. [April 2009]
2008's Jury president of Cannes Film Festival.
In October 2008, he traveled to Cuba where he met with and interviewed President Raúl Castro.
Requested to withdraw the papers he filed for legal separation from Robin Wright. [May 2009]
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]
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]
Flew to Haiti on January 21 2010 to help the relief effort after the earthquake.
Visited Egypt and Libya. [October 2011]
Ranks his good friend Philip Seymour Hoffman as one of the greatest actors of his generation (interview: "Piers Morgan Tonight: Episode dated 14 October 2011" (2011)).
Has openly declared that he'd much rather direct movies than act in them (interview: "Piers Morgan Tonight: Episode dated 14 October 2011" (2011)).