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01
Robert De Niro is a close friend of Sean Penn. They share the same birthday, August 17, and have celebrated together with joint parties.
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02
In 1987, Penn served 32 days in jail for assaulting an extra on a film set.
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03
In At Close Range 1986, Penn acted alongside his brother Chris Penn, and their mother Eileen Ryan played their grandmother.
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04
In 2009, Penn completed 300 hours of community service and 36 hours of anger management after being charged with misdemeanor vandalism for kicking a paparazzi in the leg.
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05
Christopher Nolan and Warner Bros. first choice for the Joker in The Dark Knight 2008 was Sean Penn, but he turned it down because he did not want to play a role already played by his friend Jack Nicholson. Heath Ledger eventually took the part.
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06
Penn quit smoking for a while on his 40th birthday for health reasons. He was one of Hollywood’s heaviest smokers, smoking at least four packs a day.
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07
In October 2002, Penn bought a $56,000 ad in the Washington Post to publish an open letter to President George W. Bush urging caution about moving toward war in Iraq. He wrote it as a father of two and a son of a WWII veteran.
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08
Penn refuses to discuss his ex-wife Madonna in interviews. On her 1989 album Like a Prayer, she wrote a song about their failed marriage called Till Death Do Us Part. Penn signed a prenuptial agreement and received no financial support.
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09
His son Hopper is named after family friends Dennis Hopper and Jack Nicholson.
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10
Penn flew to Haiti on January 21, 2010 to assist with relief efforts after the earthquake.
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11
He is the 9th person to win two Academy Awards for Best Actor.
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12
Penn moved to Marin County, north of San Francisco, to avoid raising his children in Hollywood.
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13
He and Robin Wright lived together off and on for seven years and had two children before marrying in 1996.
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14
In January 2016, Rolling Stone published an interview Penn conducted with fugitive drug kingpin El Chapo while he was still at large. Penn was criticized by the Obama administration and investigated by the Mexican government for not aiding authorities.
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15
Penn was in the same acting class as Michelle Pfeiffer in the late 1970s or early 1980s.
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16
He ranked his friend Philip Seymour Hoffman as one of the greatest actors of his generation in a 2011 interview.
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17
Penn met Robin Wright on the set of State of Grace 1990.
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18
His 1987 Buick Grand National was stolen in Berkeley after his return from Iraq; two guns were among the lost contents.
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19
His performance as Jeff Spicoli in Fast Times at Ridgemont High 1982 is ranked #9 on Premiere’s 100 Greatest Movie Characters of All Time.
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20
As of 2005, Penn is the only actor besides Woody Allen himself to receive a Best Actor nomination for a Woody Allen film.
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21
Penn credits Malcolm McDowell as the best actor he has worked with. They co-starred in Hugo Pool 1997.
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22
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, and he served part of it in a private jail facility.
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23
His paternal grandparents were Ashkenazi immigrants from Russia and Lithuania. They ran a deli in New York. His mother’s heritage is half Italian and half Irish.
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24
His father, Leo Penn, was blacklisted in the 1950s for his political beliefs.
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25
Andy Warhol attended Penn’s wedding to Madonna on August 16, 1985.
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26
He and Madonna’s birthdays are a day apart. They married on her 27th birthday; he turned 25 the next day.
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27
Penn is one of four people to have won acting prizes at Venice, Cannes, and Berlin film festivals, along with Julianne Moore, Juliette Binoche, and Jack Lemmon, all of whom also won acting Oscars.
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28
He is good friends with Metallica drummer Lars Ulrich.
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29
Penn was briefly engaged to actress-photographer Pamela Springsteen, sister of Bruce Springsteen. Both appeared in Fast Times at Ridgemont High 1982.
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30
He has been criticized for calling for more gun control while admitting he owns guns.
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31
Penn discussed possibly starring in Blood Work 2002 with Clint Eastwood, but it fell through. They later worked together on Mystic River 2003.
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32
He is an avid surfer.
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33
Six films starring Penn were nominated for Best Picture Oscar: The Thin Red Line 1998, Mystic River 2003, Milk 2008, The Tree of Life 2011, Licorice Pizza 2021, and One Battle After Another 2025, won.
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34
Penn lost out to Christopher Atkins for the role of Richard in The Blue Lagoon 1980 on the final day of auditions.
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35
He moved his family from Hollywood to Marin County because he was tired of a lot of aspects of Los Angeles, the main one being raising the kids in a company town.
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36
His home was lost in the Malibu fire in November 1993.
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37
He has two children with Robin Wright: daughter Dylan born April 13, 1991 and son Hopper born August 6, 1993.
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38
In October 2008, Penn traveled to Cuba and interviewed President Raúl Castro.
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39
He filed for divorce from Robin Wright a year after they reconciled following her filing in late 2007.
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40
Penn is a practitioner of Jeet Kune Do.
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41
He has openly stated he prefers directing to acting 2011 interview.
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42
He founded CORE Community Organized Relief Effort.
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43
Robin Wright filed for divorce after 11 years of marriage on December 21, 2007, citing irreconcilable differences; the couple withdrew the petition in April 2008.
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44
Penn directed one Oscar-nominated performance: Hal Holbrook in Into the Wild 2007.
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45
He was considered for the role of Martin Riggs in Lethal Weapon 1987 and Batman in Batman 1989.
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46
He has worked with eight directors who have won Best Director Oscars: John Schlesinger, Oliver Stone, Woody Allen, Kathryn Bigelow, Clint Eastwood, Alejandro G. Iñárritu, Sydney Pollack, and Barry Levinson.
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47
His fourth film as director was Into the Wild 2007, a biopic about Chris McCandless. His former wife Robin Wright filmed a similar theme in her directorial debut Land 2021.
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48
Penn was engaged to Elizabeth McGovern, whom he met on the set of Racing with the Moon 1984.
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49
The longest he has gone without an Oscar nomination is five years, between Mystic River 2003 and Milk 2008.
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50
On September 11, 2004, he received the John Steinbeck Award at the Palace of Fine Arts in San Francisco, presented by Bruce Springsteen, with film clips and discussion with Peter Coyote.
