Penn appeared in a 1974 episode of theLittle House on the Prairie television series as an extra when his father, Leo, directed some of the episodes.[16] Penn launched his film career with the action-dramaTaps (1981), where he played a military high school cadet.[15] That same year he made hisBroadway debut in the Kevin Heelan playHeartland at theCentury Theatre.[17] A year later, he appeared in the hit comedyFast Times at Ridgemont High (1982), in the role of surfer-stoner Jeff Spicoli; his character helped popularize the word "dude" in popular culture.[15] Next, Penn appeared as Mick O'Brien, a troubled youth, in the dramaBad Boys (1983).[15] The role earned Penn favorable reviews and jump-started his career as a serious actor. He returned to Broadway that same year acting in theJohn Byrne playSlab Boys acting alongsideKevin Bacon,Val Kilmer,Jackie Earl Haley, andMadeleine Potter at thePlayhouse Theatre.[18]
Penn playedAndrew Daulton Lee in the filmThe Falcon and the Snowman (1985), which closely followed an actual criminal case.[15] Lee was a former drug dealer, convicted of espionage for theSoviet Union and originally sentenced to life in prison, but was paroled in 1998. Penn later hired Lee as his personal assistant, partly because he wanted to reward Lee for allowing him to play Lee in the film; Penn was also a firm believer in rehabilitation and thought Lee should be successfully reintegrated into society, since he was a free man again.[19] Penn starred in the dramaAt Close Range (1986) which received critical acclaim.[15] He stopped acting for a few years in the early 1990s, having been dissatisfied with the industry, and focused on making his directing debut.[15]
In 2018 Penn starred in his first leading role in a television series portraying Tom Hagerty, an astronaut chosen to be one of the first people to visitMars in theHulu science fiction drama seriesThe First created byBeau Willimon.[68] Daniel Fienberg ofThe Hollywood Reporter wrote of his performance, "You can quickly see why Penn gravitated toward this as his series debut. His physical transformation and high-intensity confrontations...are showy, but the slowly unfolding role also lets him play quiet moments, and even light ones" adding, "It's funny that I'm always surprised by how game Penn is to be a goofball. The guy who starred inFast Times at Ridgemont High is still in there somewhere."[69] The series received positive reviews[70] but on January 18, 2019, Hulu canceled the series after one season.[71] In 2020 Penn played himself in a cameo role in theCurb Your Enthusiasmseason 10 episode "The Spite Store".[72]
In 2023 Penn directed his first documentary film,Superpower, profiling thePresident of UkraineVolodymyr Zelenskyy which premiered at theBerlin International Film Festival.[77][78] The film follows Penn as he travels toUkraine to meet with Zelenskyy, the soldiers and observe firsthand how theRusso-Ukrainian War is being waged.[79] Penn starred as a cab driver in Christy Hall's directorial debutDaddio (2023) acting oppositeDakota Johnson. Film critic Todd McCarthy ofDeadline Hollywood wrote, "Sean Penn is at his absolute best here in a tremendously engaging performance as a salty working-class guy with an endless supply of opinions and ways of drawing out his passengers".[80]
In 2025, he appeared on theNetflix late-night talk showEverybody's Live with John Mulaney alongsideAdam Sandler. Penn and Sandler give Mulaney advice for the physical fight he would later have with three 14-year olds on the show.[81] The same year, he reunited with Paul Thomas Anderson, starring in his filmOne Battle After Another as the main antagonist.[82] Penn also appeared in the Ukrainiananthology filmWar Through the Eyes of Animals, portraying a sound producer at the start of the2022 Russian invasion of Ukraine in the act "The Eagle"; he offered to be in the movie for just $1 since the Screen Actors Guild forbids its members from working for free.[83]
Personal life
Marriages and relationships
Penn with then-wifeRobin Wright in September 2006; the two were married from 1996 to 2010.
Penn met singer-songwriterMadonna on set of her "Material Girl" music video in January 1985.[86] On August 16, 1985, they married on Madonna's 27th birthday; Penn turned 25 the next day.[87] The two starred in the pannedShanghai Surprise (1986), directed byJim Goddard, and Madonna dedicated her third studio albumTrue Blue (1986) to Penn, referring to him in the liner notes as "the coolest guy in the universe".[88] Their marriage was marred by Penn's violent outbursts against the press.[89] Madonna filed for divorce in December 1987, but withdrew the papers two weeks later.[90] In January 1989, Madonna filed for divorce again and reportedly withdrew an assault complaint against Penn following an incident at theirMalibu, California, home during the New Year weekend.[91][92] Penn was alleged to have struck Madonna on multiple occasions during their marriage in the bookMadonna Unauthorized.[93] Madonna denied the allegations stating they were "completely outrageous, malicious, reckless, and false" in 2015.[94][86]
In 1989, Penn began dating actressRobin Wright, and their first child, a daughter namedDylan Frances, was born April 13, 1991.[95] Their second child, sonHopper Jack, was born August 6, 1993.[96] Penn and Wright separated in 1995, during which time he developed a relationship withJewel, after he spotted her performing onLate Night with Conan O'Brien. He invited her to compose a song for his filmThe Crossing Guard (1995) and followed her on tour.[97] Penn reconciled with Wright and they married on April 27, 1996. The couple filed for divorce in December 2007 but reconciled several months later, requesting a court dismissal of their divorce case.[98] In April 2009, Penn filed for legal separation, only to withdraw the case once again when the couple reconciled in May.[99][100][101] On August 12, 2009, Wright filed for divorce again.[102][103] The couple's divorce was finalized on July 22, 2010; the couple reached a private agreement on child and spousal support, division of assets, and custody of Hopper, who was almost 17 at the time.[104]
In December 2013, Penn began dating South African actressCharlize Theron.[105] Their relationship ended in June 2015.[106] Despite reports that they were engaged, Theron stated that they were never engaged.[107] Theron starred in Penn's filmThe Last Face (2016), which they filmed while still a couple.[105]
In 2016, Penn began a relationship with Australian actressLeila George, daughter of actorsVincent D'Onofrio andGreta Scacchi.[108] They married on July 30, 2020.[109] George filed for divorce on October 15, 2021.[110] Their divorce was finalized on April 22, 2022.[111] In June 2023, Penn began a relationship with Ukrainian Olga Korotyayeva.[112]
Legal issues
In October 1985, Penn pled no contest to charges that he assaulted two journalists when they tried to photograph him and Madonna in Nashville in June 1985.[113] He was fined $50 on each of two misdemeanor charges of assault and battery.[113] In January 1986, Penn was charged for allegedly assaulting Leonel Borralho,Macau correspondent for theHong Kong Standard newspaper, after he photographed Madonna and Penn as they arrived at their hotel room.[114] In June 1986, Penn was charged with misdemeanor battery for assaulting songwriterDavid Wolinski at Helena's nightclub in Los Angeles.[115] Wolinski said Penn accused him of trying to kiss Madonna. Penn pled not guilty to the charge.[116]
In April 1987, Penn violated probation and was arrested for punching a film extra, Jeffrey Klein, on set of the movieColors.[117] Penn was sentenced to 60 days in jail for this assault and reckless driving in June 1987, of which he served 33 days.[118][119] According to Penn himself, he was incarcerated in the same jail holdingRichard Ramirez, a serial killer awaiting trial. Ramirez wrote to Penn, to which Penn wrote back saying he had no kinship for his fellow inmate and hopes Ramirez receivescapital punishment via thegas chamber.[120] In May 2010, Penn pleaded no contest to a misdemeanor charge stemming from an altercation with photographer Frank Mateljan in October 2009.[121] He was sentenced to perform 300 hours of community service and undergo 36 hours of anger management counseling.[122]
In an interview published September 16, 2015, director and showrunnerLee Daniels responded to criticism aboutTerrence Howard's continued career in light of his domestic violence issues by referencing Penn's rumored history of domestic violence, saying: "[Terrence] ain't done nothing different thanMarlon Brando or Sean Penn, and all of a sudden he's some f—in' demon."[123] In response, Penn launched a $10 million defamation suit against Daniels, alleging that he had never been arrested for or charged with domestic violence.[124] Penn dropped the lawsuit in May 2016 after Daniels retracted his statement and apologized.[125]
In August 2008, Penn attended one ofRalph Nader's "Open the Debates" super rallies, protesting against Nader and other third-party candidates's exclusion.[131] In October 2008, Penn visitedCuba, where he met with and interviewed thenCuban presidentRaúl Castro.[132]
In the letter, Penn also criticized the Bush administration for its "deconstruction ofcivil liberties" and its "simplistic and inflammatory view of good and evil."[135] Penn visited Iraq briefly in December 2002.[134] The criticism drew praise from Penn's ex-wifeMadonna, who said, "Sean is one of the few. Good for him. Most celebrities are keeping their heads down. Nobody wants to be unpopular. But then Americans, by and large, are pretty ignorant of what's going on in the world."[136]
ThePost advertisement was cited as a primary reason for the development of his relationship with Venezuelan presidentHugo Chávez. In one of his televised speeches, Chávez used and read aloud an open letter Penn wrote to Bush.[137] The letter condemned theIraq War, called for Bush to beimpeached, and also called then US Vice PresidentDick Cheney and US Secretary of StateCondoleezza Rice "villainously and criminally obscene people."[138]
On April 19, 2007, Penn appeared onThe Colbert Report and had a "Meta-Free-Phor-All" versusStephen Colbert that was judged byRobert Pinsky following Penn's criticisms of Bush. In the appearance, Penn said, "We cower as you point your fingers telling us to support our troops. You and the smarmy pundits in your pocket– those who bathe in the moisture of your soiled and blood-soaked underwear–can take that noise and shove it."[139] He won the contest with 10,000,000 points to Colbert's 1.[140]
On December 7, 2007, Penn said he supported Ohio CongressmanDennis J. Kucinich in the2008 US presidential election, and again criticized Bush's handling of the Iraq War. Penn questioned whether Bush's daughters,Jenna andBarbara, supported the war in Iraq.[141]
Natural disasters
In September 2005, Penn traveled toNew Orleans, to aidHurricane Katrina victims. He was physically involved in rescuing people,[142] although there was criticism that his involvement was a PR stunt as he hired a photographer to come along with his entourage.[143] Penn denied such accusations in an article he wrote forHuffPost.[144] DirectorSpike Lee interviewed Penn for Lee's documentary about Hurricane Katrina,When the Levees Broke: A Requiem in Four Acts (2006).
After the2010 Haiti earthquake, Penn founded theJ/P Haitian Relief Organization,[145] which operated a 55,000 person tent camp.[146] Prior to founding the organization, Penn acknowledged he had never visitedHaiti and did not speak French orCreole. When asked about critics who questioned his experience on Haiti, he said he hopes they "die screaming ofrectal cancer".[147]
On January 31, 2012, due largely to his visibility as an on-the-ground advocate for rescue and aid efforts in the aftermath, Penn was designated by thenHaitian presidentMichel Martelly as Ambassador-at-Large for Haiti, the first time a non-Haitian citizen has held the position in the country's history.[148] Also in 2012, at the 12th World Summit of Nobel Peace Laureates, Penn was recognized with the Peace Summit Award.[149]
Gender and sexual orientation
On February 22, 2009, Penn received theAcademy Award for Best Actor for the filmMilk. In his acceptance speech, he said: "I think that it is a good time for those who voted for the ban against gay marriage to sit and reflect and anticipate their great shame and the shame in their grandchildren's eyes if they continue that way of support. We've got to have equal rights for everyone!"[150] In 2022, Penn expressed his position on masculinity, saying, "I am in the club that believes that men in American culture have become wildly feminised...I don't think that [in order] to be fair to women, we should become them." He later toldThe Independent that "I think that men have, in my view, become quite feminised...There are a lot of, I think, cowardly genes that lead to people surrendering their jeans and putting on a skirt."[151]
International affairs
Penn gained significant attention inPakistan media when he visitedKarachi andBadin in 2012. On March 23, 2012, accompanied by US Consul General William J. Martin, Penn visited flood-stricken villages in Karim Bux Jamali, Dargah Shah Gurio, and Peero Lashari in theBadin District, where he distributed blankets, quilts, kitchen items, and other goods to flood survivors.[152][153]
On March 24, 2012, during his visit to Pakistan, Penn visited Bilquis Edhi Female Child Home and met Pakistani humanitarian workerAbdul Sattar Edhi and his wifeBilquis Edhi and laid floral wreaths at the shrine ofAbdullah Shah Ghazi in honor of him.[154][155]
Penn is also believed to have played a role in securing the release of American entrepreneurJacob Ostreicher from a Bolivian prison in 2013, and was credited by Ostreicher for having personally nursed him back to health after his release.[156]
In October 2021, theNational Labor Relations Board filed a complaint that Penn and CORE violatedUS federal labor law, contending that Penn "impliedly threatened" his employees with reprisals after they complained about working conditions, which allegedly included 18-hour work days.[158]
Penn and Chávez maintained a friendship; when Chávez died in 2013, Penn said: "Venezuela and its revolution will endure under the proven leadership of Vice PresidentNicolás Maduro. Today the United States lost a friend it never knew it had. And poor people around the world lost a champion. I lost a friend I was blessed to have."[164] Penn's friendship with Chávez and his praise for Cuban dictatorRaúl Castro have been criticized by human rights activistThor Halvorssen and media, includingThe New York Times, theLos Angeles Times,The New Criterion, andThe Advocate, each of which alleged that Castro and Chávez's strong anti-LGBT stances clashed with Penn's support for LGBT groups.[165][166][167][168] ActressMaría Conchita Alonso, who co-starred with Penn inColors, also issued an "Open Letter to Sean Penn", attacking his views on Chávez.[169] In December 2011, Alonso and Penn began verbally fighting at an airport, during which Penn called her "a pig" and Alonso called Penn acommunist.[170]
Mexico
On January 9, 2016, a day after Mexican officials announced the capture of fugitiveSinaloa Cartel bossJoaquín "El Chapo" Guzmán in a militarized raid,Rolling Stone reported that Penn and actressKate del Castillo had conducted a secret interview with El Chapo prior to his arrest.[171][172] Del Castillo was contacted by Guzmán's lawyer, who was then underCISEN surveillance, to discuss producing a biographical film about Guzmán, and communication between the two increased following Guzmán's escape from a Mexican prison in July 2015.[173] The deal for the interview was brokered by del Castillo.[174]
According to text messages released between Penn and del Castillo, El Chapo did not know who Sean Penn was.[175] CISEN released photographs of del Castillo at the meetings with Guzmán's lawyers and of Penn and del Castillo arriving in Mexico. The interview was criticized byWhite House, which called it "maddening".[176] Mexican authorities said they sought to question Penn over the interview, which had not been approved by either the American or Mexican government.[177] Penn and del Castillo's meeting with Guzmán was investigated by theAttorney General of Mexico.[178] Del Castillo acknowledged that she never resumed communication with Penn after the release of theRolling Stone article.[179] In October 2025, Del Castillo harshly criticized Penn, calling him "scum" and accusing him of using her as "bait" during their 2015 meeting with Guzmán. Penn had never told her that he had planned to write the article despite her central role in arranging the meeting.[180]
In 2022, Penn visitedUkraine to film a documentary about theRussian invasion of that country.[182] Penn attended press briefings inKyiv, met with officials and spoke to journalists and military personnel about the Russian invasion.[183][182] On February 25, 2022, Penn said, "If we allow it [Ukraine] to fight alone, our soul as America is lost."[183]
Penn also praised the response from the Ukrainian government and its citizens.[183] As Penn and his team prepared to leave Ukraine, they abandoned their car and walked with their luggage for miles to the Polish border.[184] Russia is sanctioning Penn over his Ukraine support.[185]
In February 2012, Penn met with thePresident of Argentina,Cristina Fernández de Kirchner, inBuenos Aires, where he commented on the long-runningdispute between Argentina and the United Kingdom over theFalkland Islands, saying: "I know I came in a very sensitive moment in terms of diplomacy between Argentina and the UK over the Falkland Islands. And I hope that diplomats can establish true dialogue in order to solve the conflict as the world today cannot tolerate ridiculous demonstrations of colonialism. The way of dialogue is the only way to achieve a better solution for both nations."[187][188][189]
The comments were taken as support of Argentina's claim to the islands and evoked reactions in British media, including a satirical article inThe Daily Telegraph requesting that Penn "return his Malibu estate to theMexicans".[190]
In February 2012, Penn's comments on the Falklands dispute were criticized byFalklands War veteran and political activistSimon Weston, who said, "Sean Penn does not know what he is talking about and, frankly, he should shut up. His [Penn's] views are irrelevant and it only serves to fuel the fire of the Argentinians and get them more pumped up."[191]British Conservative MPPatrick Mercer called Penn's statement on the Falklands "moronic".[192] Lauren Collins wrote inThe New Yorker, "As of today, Sean Penn is the newKarl Lagerfeld—the man upon whom, having disrespected something dear to the United Kingdom, the British papers most gleefully pile contempt".[193]
Penn later claimed his comments were misrepresented in British press and that his criticism of "colonialism" was a reference to the deployment ofPrince William as an air-sea rescue pilot, describing it as a "message of pre-emptive intimidation". He claimed that the Prince's posting meant "the automatic deployment of warships", and stated: "My oh my, aren't people sensitive to the word 'colonialism', particularly those who implement colonialism."[194][195]
In an op-ed written inThe Guardian, Penn wrote that "the legalisation of Argentinian immigration to the Malvinas/Falkland Islands is one that it seems might have been addressed, but for the speculative discovery of booming offshore oil in the surrounding seas this past year" and that it was "irresponsible journalism" to suggest "that I had taken a specific position against those currently residing in the Malvinas/Falkland Islands, that they should either be deported or absorbed into Argentine rule. I neither said, nor insinuated that".[195][196]
^"Sean Penn".Biography.com. A&E Television Networks. RetrievedAugust 14, 2020.Sean Justin Penn was born on August 17, 1960, in Santa Monica, California. His father, Leo, was an actor and director. His mother, Eileen Ryan, was an actress. Penn grew up in Los Angeles and attended Santa Monica High School along with fellow students and future actors Emilio Estevez, Charlie Sheen and Rob Lowe ...
^Anderson, Paul Thomas (September 26, 2025),One Battle After Another (Action, Crime, Drama), Leonardo DiCaprio, Sean Penn, Benicio Del Toro, Ghoulardi Film Company, Warner Bros., retrievedSeptember 27, 2025
^MacMinn, Aleene (April 17, 1991)."Cradle Watch".Los Angeles Times.Archived from the original on March 9, 2012. RetrievedJuly 27, 2014.Dylan Frances Penn was born Saturday [April 13] at 10:49 p.m. at UCLA Medical Center.
^Speidel, Maria (August 23, 1993)."Passages".People.Archived from the original on March 16, 2017. RetrievedMarch 16, 2017.
^Penn, Sean (2018).Bob Honey Who Just Do Stuff: A Novel (1st Atria Books hardcover ed.). New York: Atria Books.ISBN9781501189043.OCLC1000331844.
^Penn, Sean (2019).Bob Honey Sings Jimmy Crack Corn: A Novel (1st hardcover ed.). Los Angeles, California: Rare Bird Books.ISBN9781644280584.OCLC1096458844.
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