Trivia

Is very good friends with Robert De Niro. The two share the same birthday and would often throw a joint birthday party together.

He served 32 days in jail in 1987 for hitting an extra.

Appeared with his brother Chris Penn in At Close Range (1986), in which their actress mother, Eileen Ryan, played their grandmother.

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)

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". Penn signed a prenuptial agreement and received no financial support.

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.

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 son is named after two family friends, Dennis Hopper and Jack Nicholson.

He was Christopher Nolan and Warner Bros. first choice for the role of the Joker for the movie "The Dark Knight (2008)", but he turned down the part because he didn't want to play a role that had already been played by his longtime friend Jack Nicholson. The role ultimately went to Heath Ledger.

He is the 9th person to win 2 Academy Awards for Best Actor.

Moved to Marin County (north of San Francisco) to avoid raising his children in Hollywood.

Flew to Haiti on January 21, 2010 to help the relief effort after the earthquake.

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.

He and Robin Wright lived together off and on for 7 years and had two children before their marriage in 1996.

Ranks his good friend Philip Seymour Hoffman as one of the greatest actors of his generation (interview: Episode dated 14 October 2011 (2011)).

Was in the same acting class as Michelle Pfeiffer at the end of the '70s or early '80s.

As of 2005, the only actor to ever receive a Best Actor nomination for a Woody Allen film, besides Allen himself.

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.

His father, Leo Penn, had been blacklisted in the 1950s for his political beliefs.

In January, 2016, shortly after the recapture of the notorious fugitive drug kingpin "El Chapo" (Joaquín Guzmán Loera), Rolling Stone magazine published an interview with him that Sean Penn conducted during the time the Sinaloa drug cartel head was still at large ("El Chapo" had escaped from a Mexican maximum-security prison in 2015). Guzmán contacted Penn via a Mexican movie and TV star, Kate del Castillo, who, after playing a drug kingpin in the Mexican TV show La Reina del Sur (2011), had been contacted by Guzmán in the hope that she would make a movie about his life. After his interview was published, Penn was criticized by the Obama administration and investigated by the Mexican government for failing to aid authorities in recapturing Guzmán earlier than they did.

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.

Andy Warhol was a guest during his August 16, 1985 marriage to Madonna.

Credits Malcolm McDowell as the best actor with whom he's worked. They co-starred in Hugo Pool (1997).

His paternal grandparents were Ashkenazi immigrants (their families were from Russia and Lithuania). They ran a deli in New York for some time. His mother's heritage is half Italian and half Irish.

One of four people to have achieved the rare feat of winning an acting prize in the three major film festivals: Venice Film Festivel, Cannes Film Festival and Berlin International Film Festival. The others to do so are Julianne Moore, Juliette Binoche and Jack Lemmon. Additionally, all four actors have won acting Oscars.

Briefly engaged to actress-photographer Pamela Springsteen, sister of Bruce Springsteen. The two were both in Fast Times at Ridgemont High (1982).

Met wife-to-be Robin Wright on the set of State of Grace (1990).

He and ex-wife Madonna's birthdays are a day apart. They married on her 27th birthday and he turned 25 the next day.

Good friends with Metallica drummer Lars Ulrich.

He has appeared in five films that have been nominated for the Best Picture Oscar: The Thin Red Line (1998), Mystic River (2003), Milk (2008), The Tree of Life (2011) and Licorice Pizza (2021).

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).

He was criticized for publicly calling for more gun control in the United States, despite admitting that he owned guns.

Founder of CORE: Community Organized Relief Effort.

Lost out to Christopher Atkins for the role of Richard in The Blue Lagoon (1980) on the final day of auditions.

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".

Is an avid surfer.

They lost their home in the Malibu fire in November 1993.

In October, 2008, he traveled to Cuba where he met with and interviewed President Raúl Castro.

Has 2 children: daughter, Dylan Penn (b. April 13, 1991) & son, Hopper Penn (b. August 6, 1993) with ex-wife, Robin Wright.

Filed for divorce from Robin Wright, a year after they reconciled after she had filed for divorce in late 2007. (April 2009)

Is a Practitioner of Jeet Kune Do.

A popular indie-band in The Netherlands is called "Seanpenn".

Has openly declared that he'd much rather direct movies than act in them (interview: Episode dated 14 October 2011 (2011)).

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.

He has appeared in one film that has been selected for the National Film Registry by the Library of Congress as being "culturally, historically or aesthetically" significant: Fast Times at Ridgemont High (1982).

Was considered for the role of Martin Riggs in "Lethal Weapon" (1987) & the role of Batman/Bruce Wayne in "Batman" (1989).

He has worked with 8 directors who have won a Best Director Oscar: John Schlesinger, Oliver Stone, Woody Allen, Kathryn Bigelow, Clint Eastwood, Alejandro G. Iñárritu, Sydney Pollack and Barry Levinson.

Directed one Oscar nominated performance: Hal Holbrook in Into the Wild (2007).

The longest he has gone without an Oscar nomination is 5 years, between Mystic River (2003) and Milk (2008).

Was engaged to Elizabeth McGovern. They met on the set of Racing with the Moon (1984).