| # | Fact |
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| 1 | 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. |
| 2 | 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. |
| 3 | Campaigned for John Kerry in the 2004 presidential election. |
| 4 | Publicly supported Argentina's claim to the Falkland Islands. |
| 5 | Publicly endorsed Hillary Clinton as the Democratic candidate in the 2016 US presidential election. |
| 6 | He is half-Jewish. |
| 7 | He was criticized for publicly calling for more gun control in the United States, despite admitting that he owned guns. |
| 8 | In January 2016, shortly after the recapture of the notorious fugitive drug kingpin Joaquin "El Chapo" 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 a Mexican TV show, 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. |
| 9 | His father Leo Penn, a writer was blacklisted during McCarthy era in Hollywood. |
| 10 | Is a Practitioner of Jeet Kune Do. |
| 11 | Was considered for the role of Martin Riggs in Lethal Weapon (1987) & the role of Batman/Bruce Wayne in Batman (1989). |
| 12 | Received an honorary César award in France for his body of work in 2015, Marion Cotillard presented the award to him. [20 February, 2015]. |
| 13 | In three consecutive years won acting prizes in the three major film festivals: Berlin Silver Bear Best Actor (Dead Man Walking [1995]) in 1996, Cannes Best Actor (She's So Lovely [1997]) in 1997, and Venice Volpi Cup Best Actor (Hurlyburly [1998]) in 1998 becoming the fastest among the four actors to have accomplished the feat of winning in the aforementioned film festivals. |
| 14 | 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. |
| 15 | As of 2014, has appeared in four films that were nominated for the Best Picture Oscar: The Thin Red Line (1998), Mystic River (2003), Milk (2008) and The Tree of Life (2011). |
| 16 | Attended the 2003 San Sebastian Film Festival in Spain. [September 2003] |
| 17 | Attended the Cannes Film Festival. [May 2001] |
| 18 | Attended the Cannes Film Festival. [May 2000] |
| 19 | Attended the Cannes Film Festival in France. [May 2011] |
| 20 | Attended the BFI London Film Festival (on Oct. 25th) as well as the 2nd Rome Film Festival (on Oct. 24th) to promote his film Into the Wild. [October 2007] |
| 21 | Attended the 2004 Cannes Film Festival in France. [May 2004] |
| 22 | Release of the book, "Sean Penn: His Life and Times" by Richard T. Kelly. [2004] |
| 23 | Attended the Cesar Film Awards in Paris, France on Feb. 27th. [February 2009] |
| 24 | Attended the 2008 Cannes Film Festival in France. [May 2008] |
| 25 | Attended the Venice Film Festival in Italy on Sept. 5th. [September 2003] |
| 26 | Attended the Mike Tyson vs Michael Spinks fight at Trump Plaza on June 27th in Atlantic City, New Jersey. [June 1988] |
| 27 | Directed one Oscar nominated performance: Hal Holbrook in Into the Wild (2007). |
| 28 | Was engaged to Elizabeth McGovern. They met on the set of Racing with the Moon (1984). |
| 29 | The longest he has gone without an Oscar nomination if 5 years, between Mystic River (2003) and Milk (2008). |
| 30 | Has openly declared that he'd much rather direct movies than act in them (interview: Piers Morgan Tonight: Episode dated 14 October 2011 (2011)). |
| 31 | 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)). |
| 32 | Visited Egypt and Libya. [October 2011] |
| 33 | Is the subject of the song, "Sean Penn Blues", by Lloyd Cole & The Commotions. |
| 34 | 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] |
| 35 | 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. |
| 36 | Penn's At Close Range (1986) director James Foley served as best man at Penn and Madonna's wedding (1985). |
| 37 | Flew to Haiti on January 21 2010 to help the relief effort after the earthquake. |
| 38 | Born at 3:17 PM (PDT). |
| 39 | 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] |
| 40 | His publicist is Mara Buxbaum. |
| 41 | Lost out to Christopher Atkins for the role of Richard in The Blue Lagoon (1980) on the final day of auditions. |
| 42 | Requested to withdraw the papers he filed for legal separation from Robin Wright. [May 2009] |
| 43 | Filed for divorce from Robin Wright, a year after they reconciled after she had filed for divorce in late 2007. [April 2009] |
| 44 | In October 2008, he traveled to Cuba where he met with and interviewed President Raúl Castro. |
| 45 | Is very good friends with Robert De Niro. The two share the same birthday and would often throw a joint birthday party together. |
| 46 | He is the 9th person to win 2 Academy Awards for Best Actor. |
| 47 | He and ex-wife Madonna's birthdays are a day apart. They married on her 27th birthday and he turned 25 the next day. |
| 48 | Milo Ventimiglia listed him as his favorite actor. |
| 49 | Former son-in-law of Silvio Ciccone. |
| 50 | Former brother-in-law of Christopher Ciccone, Martin Ciccone, Paula Ciccone, Anthony Ciccone, Melanie Ciccone, Mario Ciccone, and Jennifer Ciccone. |
| 51 | He toured Caracas, Venezuela, in August 2007 with President Hugo Chávez,. |
| 52 | 2008's Jury president of Cannes Film Festival. |
| 53 | Is an avid surfer. |
| 54 | 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. |
| 55 | Good friends with Metallica drummer Lars Ulrich. |
| 56 | Was in the same acting class as Michelle Pfeiffer at the end of the 70s or early 80s. |
| 57 | 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". |
| 58 | 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. |
| 59 | As of 2005, the only actor to ever receive a Best Actor nomination for a Woody Allen film, besides Allen himself. |
| 60 | Credits Malcolm McDowell as the best actor with whom he's worked. |
| 61 | Briefly engaged to actress-photographer Pamela Springsteen, sister of Bruce Springsteen. The two were both in Fast Times at Ridgemont High (1982). |
| 62 | A popular indie-band in The Netherlands is called "Seanpenn". |
| 63 | Andy Warhol was a guest during his August 16, 1985 marriage to Madonna. |
| 64 | 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). |
| 65 | 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. |
| 66 | 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". |
| 67 | His father, Leo Penn, had been blacklisted in the 1950s for his political beliefs. |
| 68 | 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. |
| 69 | His paternal grandparents were Ashkenazi Jewish immigrants (their families were from Russia and Lithuania). They ran a Jewish deli in New York for some time. His mother's heritage is half Italian and half Irish. |
| 70 | 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. |
| 71 | 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. |
| 72 | Brother-in-law of Aimee Mann. |
| 73 | His son is named after two family friends, Dennis Hopper and Jack Nicholson. |
| 74 | Became a father for the 2nd time at age 32 when his girlfriend [now 2nd ex-wife] Robin Wright gave birth to their son Hopper Penn on August 6, 1993. |
| 75 | Became a father for the 1st time at age 30 when his girlfriend [now 2nd ex-wife] Robin Wright gave birth to their daughter Dylan Penn on April 13, 1991. |
| 76 | Moved to Marin County (North of San Francisco) to avoid raising his children in Hollywood. |
| 77 | Middle brother of musician Michael Penn and Chris Penn. |
| 78 | Son of Leo Penn and Eileen Ryan. |
| 79 | Ranked #76 in Empire (UK) magazine's "The Top 100 Movie Stars of All Time" list. [October 1997] |
| 80 | Listed as one of twelve "Promising New Actors of 1984" in John Willis' Screen World, Vol. 36. |
| 81 | Appeared with his brother Chris Penn in At Close Range (1986), in which their actress mother, Eileen Ryan, played their grandmother. |
| 82 | They lost their home in the Malibu fire in November 1993. |
| 83 | He and Robin Wright lived together off and on for 7 years and had two children before their marriage in 1996. |
| 84 | He served 32 days in jail in 1987 for hitting an extra. |
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