Sean Penn
In Kyiv in November 2022, Sean Penn handed an Oscar statuette to Ukrainian president Volodymyr Zelenskyy. "This is for you. It's just a symbolic silly thing...When you win, bring it back to Malibu." That was the whole speech. Penn is an American actor and filmmaker whose career is built on intense, high-voltage performances. Few performers would carry a golden trophy into a country at war. Fewer still would treat it as a loan. The gesture raises questions that run through his whole career. How did a boy from a Malibu home become one of the most decorated actors of his era? Why does he keep stepping behind the camera, onto the page and into disaster zones? And why do his political stands draw such fury alongside the praise?
Sean Justin Penn was born on the 17th of August 1960 in Santa Monica, California. His father, Leo Penn, was an actor and director. His mother, Eileen Ryan, was an actress. An older brother, Michael, became a musician. A younger brother, Chris, became an actor and died in 2006. Leo was the son of emigrants from Merkinė in Lithuania, and Eileen was a Catholic of Irish and Italian descent. The household in Malibu was secular, and Penn attended Malibu Park Junior High School and then Santa Monica High School.
Emilio Estevez and Charlie Sheen lived near the Penn home, and the future actors joined other childhood friends in making short films with him. In 1974, Penn turned up as an extra in an episode of Little House on the Prairie, because his father was directing some of the episodes. His feature film debut came in 1981 with Taps, in which he played a cadet at a military high school. That same year he made his Broadway debut in Heartland, a play by Kevin Heelan staged at the Century Theatre.
Fast Times at Ridgemont High, a hit comedy of 1982, gave Penn the part of Jeff Spicoli, a surfer and stoner. The character helped popularize the word "dude". A year later came Bad Boys, in which Penn played Mick O'Brien, a troubled youth. Reviews were favorable, and the role launched him as a serious actor. He returned to Broadway that year in John Byrne's Slab Boys at the Playhouse Theatre. His fellow cast members included Kevin Bacon, Val Kilmer, Jackie Earl Haley and Madeleine Potter.
In The Falcon and the Snowman, released in 1985, Penn played Andrew Daulton Lee. Lee was a former drug dealer convicted of espionage for the Soviet Union, and the film followed a real criminal case. He was first sentenced to life in prison and was paroled in 1998. Penn later hired him as a personal assistant, partly to thank him for allowing the portrayal. Penn also believed strongly in rehabilitation and wanted Lee reintegrated into society.
At Close Range, from 1986, earned critical acclaim. Then, in the early 1990s, Penn stopped acting for a few years. He was unhappy with the industry and wanted to focus on directing. His first film as a director began with a song by Bruce Springsteen.
In 1990, Penn played Detective Terry Noonan in the neo-noir State of Grace, working opposite Ed Harris and Gary Oldman. After his break from acting, he returned for Carlito's Way in 1993. Brian De Palma directed the crime drama, and Al Pacino led the cast. Penn played Carlito's ambitious and amoral lawyer. Leonard Klady of Variety wrote that Penn reminded viewers of what they had been missing, capturing the worst of the legal profession without caricature. The role earned a Golden Globe nomination for Best Supporting Actor in a motion picture.
Dead Man Walking, directed by Tim Robbins in 1995, put Penn opposite Susan Sarandon. He played a racist murderer on death row. Roger Ebert wrote, "Penn proves again that he is the most powerful actor of his generation." The performance brought Penn his first nomination for the Academy Award for Best Actor.
She's So Lovely, directed by Nick Cassavetes, paired Penn with his then-wife Robin Wright Penn. It won him the Best Actor award at the Cannes Film Festival. Lisa Schwarzbaum of Entertainment Weekly said his performance "is so full of heart and talent". The same period brought Oliver Stone's U Turn and David Fincher's mystery thriller The Game.
Hurlyburly adapted David Rabe's 1984 play, and Penn took the lead. Peter Bradshaw of The Guardian wrote that Penn ended up dominating the film, "sweating anxiety and rage from every pore". The role won him the Volpi Cup for Best Actor at the Venice International Film Festival. Terrence Malick then cast him in The Thin Red Line, an epic about the World War II battle for Guadalcanal. It was based on the 1962 novel of the same name by James Jones.
In 1999, Woody Allen's Sweet and Lowdown gave Penn an egotistical jazz guitarist to play. Ebert described his performances as "master classes in the art of character development". The role brought his second Best Actor nomination. A third was only two years away, for a part as a father.
In the eighth season of Friends, Penn made two guest appearances as Eric, a man engaged to Phoebe Buffay's sister Ursula. Lisa Kudrow played both sisters. That same year, 2001, he took on a more serious part in I Am Sam, playing a father with an intellectual disability. It earned him a third Best Actor nomination.
Clint Eastwood's Boston crime drama Mystic River arrived in 2003. Penn played a grieving father searching for his daughter, alongside Tim Robbins, Laura Linney, Marcia Gay Harden and Kevin Bacon. Todd McCarthy of Variety wrote, "Penn is in top form as the reformed hood whose basic instincts overtake him." Penn won the Academy Award, the Critics' Choice Movie Award and the Golden Globe Award, all for Best Actor. He was also nominated for a BAFTA and a Screen Actors Guild Award. That year he also appeared opposite Naomi Watts and Benicio del Toro in Alejandro González Iñárritu's 21 Grams, which brought another BAFTA nomination.
In The Assassination of Richard Nixon, released in 2004, Penn played Samuel Bicke. The character was based on Samuel Byck, who tried and failed to assassinate President Nixon in 1974. The same year, Penn was invited to join the Academy of Motion Picture Arts and Sciences. His next big swing missed. In All the King's Men, he played governor Willie Stark, a figure based on Huey Long, in an adaptation of Robert Penn Warren's 1946 novel. The film was a critical and commercial failure. A 2010 Forbes article named it the biggest flop of the previous five years.
In November 2008, Gus Van Sant's Milk gave Penn the role of Harvey Milk, the politician and gay rights activist. Kirk Honeycutt of The Hollywood Reporter wrote that Penn was an actor in complete control of his entire instrument. Penn won his second Best Actor Oscar and the Screen Actors Guild Award for the part. Accepting the Oscar on the 22nd of February 2009, he urged voters who had backed the ban on gay marriage to reflect on their future shame, and called for equal rights.
Fair Game, from 2010, cast Penn as Joseph C. Wilson. His wife, Valerie Plame, played by Naomi Watts, was outed as a CIA agent by Bush advisor Scooter Libby. The outing came in retaliation for an article in which Wilson debunked a claim that Iraq was building a nuclear bomb. The film drew on Plame's 2007 memoir. Penn reunited with Terrence Malick for The Tree of Life, which won the Palme d'Or at the 2011 Cannes Film Festival. In Paolo Sorrentino's This Must Be the Place, he played Cheyenne, a former rock star, opposite Frances McDormand. Todd McCarthy, now writing for The Hollywood Reporter, said the performance "slithers between the genuine and the stunt-like".
In The Gunman, released in 2015, Penn played Jim Terrier, a sniper on a mercenary assassination team. Terrier kills the minister of mines of the Congo. Idris Elba, Ray Winstone, Mark Rylance and Javier Bardem filled out the supporting cast. In 2018 Penn took his first leading role in a television series. The Hulu drama The First, created by Beau Willimon, cast him as Tom Hagerty, an astronaut chosen for one of the first trips to Mars. Daniel Fienberg of The Hollywood Reporter wrote that "The guy who starred in Fast Times at Ridgemont High is still in there somewhere." Hulu canceled the show on the 18th of January 2019, after one season. In 2020 Penn played himself in the Curb Your Enthusiasm episode "The Spite Store".
Licorice Pizza, from 2021, had Penn play Jack Holden, an actor based on William Holden, for director Paul Thomas Anderson. In the Starz limited series Gaslit, in 2022, he played John N. Mitchell opposite Julia Roberts as Martha Mitchell. The role required transformational prosthetics. Ben Travers of IndieWire singled out his speech, with curse words spat out while he clenched a wooden pipe. The performance earned a Hollywood Critics Association nomination. In 2023, Daddio cast him as a cab driver opposite Dakota Johnson, in Christy Hall's directorial debut. Todd McCarthy, writing for Deadline Hollywood, called it a tremendously engaging performance as a salty, opinionated working-class man.
In 2025, Penn appeared on the Netflix talk show Everybody's Live with John Mulaney, alongside Adam Sandler. The two gave Mulaney advice about a physical fight he would later have on the show with three 14-year-olds. Penn also reunited with Paul Thomas Anderson for One Battle After Another. He played the main antagonist, Steven J. Lockjaw, a corrupt military officer. He won a British Academy Film Award, an Actor Award and the Academy Award for Best Supporting Actor, and was nominated for a Golden Globe and a Critics' Choice award. The win made him one of only four men to receive three Academy Awards for acting, alongside Walter Brennan, Jack Nicholson and Daniel Day-Lewis.
Penn has appeared in over 50 films. He received the Honorary César in 2015 and the Bob Hope Humanitarian Award in 2022. Among his most unusual fees was a single dollar. For the Ukrainian anthology film War Through the Eyes of Animals, he played a sound producer at the start of the 2022 Russian invasion, in an act called "The Eagle". He offered to work for $1 because the Screen Actors Guild forbids its members to work for free.
Bruce Springsteen's song "Highway Patrolman", from the 1982 album Nebraska, supplied the story for The Indian Runner. The 1991 crime drama was Penn's debut as a director. Janet Maslin of The New York Times wrote that Penn flirts constantly with self-indulgence yet keeps the film's "raw essence" in view. Penn directed music videos too. In 1993 he made Shania Twain's "Dance with the One That Brought You" and Lyle Lovett's "North Dakota". In 2002 he directed Peter Gabriel's "The Barry Williams Show".
The Crossing Guard followed in 1995, an indie thriller starring Jack Nicholson. Maslin called Penn "a slugger of a film maker" and praised its brute force. The Pledge, a mystery film, arrived in 2001. Into the Wild, a biographical survival drama, came in 2007. Owen Gleiberman of Entertainment Weekly wrote that Penn had written and directed with "magnificent precision and imaginative grace". Penn earned a Directors Guild of America nomination for directing it.
The Last Face, made in 2016, starred Charlize Theron and Javier Bardem. Flag Day, from 2021, starred Dylan Penn and Josh Brolin.
In March 2018, Atria Books published Penn's novel Bob Honey Who Just Do Stuff. He then went on a highly publicized press tour. He said he no longer had "a generic interest in making films" and that writing would "dominate my creative energies for the foreseeable future". A second book, Bob Honey Sings Jimmy Crack Corn, came from Rare Bird Books in 2019.
Film was not abandoned for good. In 2023, Penn directed Superpower, his first documentary. It profiled Ukrainian president Volodymyr Zelenskyy and premiered at the Berlin International Film Festival. The film follows Penn as he travels to Ukraine to meet Zelenskyy and the soldiers, and to see how the war is being fought.
On the 18th of October 2002, Penn paid $56,000 for an advertisement in The Washington Post. It was an open letter asking President George W. Bush to end military hostilities in Iraq and elsewhere. The letter attacked the administration's "deconstruction of civil liberties" and its "simplistic and inflammatory view of good and evil." Penn visited Iraq from the 13th to the 16th of December 2002, to protest apparent plans for a strike. His former wife Madonna defended him, saying, "Sean is one of the few. Good for him."
The 2004 satirical film Team America: World Police featured a puppet caricature of Penn praising Baathist Iraq. Penn answered with an angry letter to creators Trey Parker and Matt Stone, inviting them to tour Iraq with him. In June 2005 he visited Iran as a journalist on assignment for the San Francisco Chronicle, attending Friday prayer at Tehran University. On the 7th of January 2006, he joined Norman Solomon and Cindy Sheehan at an anti-war forum in Sacramento. That December, the Creative Coalition gave him the Christopher Reeve First Amendment Award for his commitment to free speech.
On the 19th of April 2007, Penn faced Stephen Colbert in a "Meta-Free-Phor-All" on The Colbert Report, judged by Robert Pinsky. Penn won, 10,000,000 points to Colbert's 1. Later that year he backed Ohio congressman Dennis J. Kucinich for president. In August 2008 he attended one of Ralph Nader's rallies protesting the exclusion of third-party candidates.
Hugo Chávez, the president of Venezuela, once read aloud one of Penn's open letters to Bush during a televised speech. The letter condemned the Iraq War, called for Bush's impeachment, and called Dick Cheney and Condoleezza Rice "villainously and criminally obscene people." The relationship grew from there. In October 2008, Penn visited Cuba and interviewed then president Raúl Castro. In March 2010 he called for jailing journalists who described Chávez as a dictator, and conservative and libertarian outlets, including National Review and Reason, criticized him. When Chávez died in 2013, Penn said poor people around the world had lost a champion and that he had lost a friend he was blessed to have. Thor Halvorssen and several newspapers noted that Chávez and Castro held strong anti-LGBT positions, which clashed with Penn's support for LGBT groups. The actress María Conchita Alonso, his co-star in Colors, published an open letter attacking his views. In December 2011 the two argued at an airport. Penn called her "a pig" and she called him a communist.
In February 2012, Penn met Argentine president Cristina Fernández de Kirchner in Buenos Aires. He said he hoped diplomats could resolve the Falkland Islands dispute through dialogue, since the world could not tolerate "ridiculous demonstrations of colonialism". British reaction was fierce. Falklands War veteran Simon Weston said Penn should be quiet. MP Patrick Mercer called the remarks "moronic". The Daily Telegraph ran a satirical piece telling Penn to return his Malibu estate to the Mexicans. Penn said the British press had misrepresented him. By "colonialism" he meant the deployment of Prince William as an air-sea rescue pilot, which he called a "message of pre-emptive intimidation". In a Guardian op-ed, he denied saying that the islands' residents should be deported or absorbed into Argentine rule.
In October 2020, Penn tweeted support for Armenia in the Nagorno-Karabakh war and endorsed Joe Biden for president. In 2021 he called cancel culture "ludicrous". In 2022 he said he belonged to the club that believes men in American culture have become wildly feminised.
On the 9th of January 2016, Rolling Stone reported that Penn and the actress Kate del Castillo had secretly interviewed the fugitive Sinaloa Cartel boss Joaquín "El Chapo" Guzmán. Guzmán had been captured a day earlier. Del Castillo had been contacted by Guzmán's lawyer to discuss a biographical film, and she brokered the meeting. Text messages released later suggested Guzmán did not know who Penn was. The White House called the interview "maddening", and Mexico's attorney general investigated. In October 2025, del Castillo called Penn "scum" and said he had used her as "bait", never telling her he planned to write the article.
In September 2005, Penn traveled to New Orleans to help victims of Hurricane Katrina. He took part in rescuing people. Critics called it a publicity stunt because he brought a photographer along with his entourage. Penn denied the charge in an article he wrote for HuffPost. Spike Lee interviewed him for the 2006 documentary When the Levees Broke: A Requiem in Four Acts.
After the 2010 Haiti earthquake, Penn founded the J/P Haitian Relief Organization. It ran a tent camp for 55,000 people. He acknowledged that he had never visited Haiti and spoke neither French nor Creole. When critics questioned his experience, he answered with a savage insult. On the 31st of January 2012, Haitian president Michel Martelly named him Ambassador-at-Large for Haiti, the first time a non-Haitian had held the post. Also in 2012, the 12th World Summit of Nobel Peace Laureates gave him its Peace Summit Award.
Penn also founded the nonprofit Community Organized Relief Effort, known as CORE. It distributed aid in Haiti after the earthquake and after Hurricane Matthew, and it ran free COVID-19 diagnostic tests in the US during the pandemic. In October 2021, the National Labor Relations Board filed a complaint against Penn and CORE. It alleged that Penn had impliedly threatened employees with reprisals after they complained about working conditions, which allegedly included 18-hour work days.
On the 23rd of March 2012, accompanied by US Consul General William J. Martin, Penn visited flood-stricken villages in Pakistan's Badin District. He handed out blankets, quilts and kitchen items in Karim Bux Jamali, Dargah Shah Gurio and Peero Lashari. The next day he visited the Bilquis Edhi Female Child Home, met humanitarian Abdul Sattar Edhi and his wife Bilquis, and laid wreaths at the shrine of Abdullah Shah Ghazi. In 2013, Penn helped secure the release of the American entrepreneur Jacob Ostreicher from a Bolivian prison. Ostreicher credited him with nursing him back to health at Penn's home.
On the 25th of February 2022, Penn said in Ukraine, "If we allow it Ukraine to fight alone, our soul as America is lost." He attended press briefings in Kyiv, met officials, and spoke with journalists and military personnel. When his team prepared to leave, they abandoned their car and walked for miles with their luggage to the Polish border. Russia is sanctioning Penn over his support. Zelenskyy awarded him the Ukrainian Order of Merit.
In March 2026, Penn visited Ukraine for the fifth time. He chose to be there instead of attending the Academy Awards ceremony, where he had been named a winner. During the stay, he received a symbolic Oscar-like statuette made from the metal of a railway car damaged in shelling.
Penn met Madonna in January 1985 on the set of her "Material Girl" music video. They married on the 16th of August 1985, her 27th birthday. Penn turned 25 the next day. The pair starred together in the panned Shanghai Surprise in 1986, and Madonna dedicated her album True Blue to him, calling him "the coolest guy in the universe". The marriage was marred by Penn's violent outbursts against the press. Madonna filed for divorce in December 1987 and withdrew the papers two weeks later. She filed again in January 1989, and reportedly withdrew an assault complaint following an incident at their Malibu home. The book Madonna Unauthorized alleged that Penn struck her on multiple occasions. In 2015, Madonna denied the allegations, calling them "completely outrageous, malicious, reckless, and false".
In 1989, Penn began dating the actress Robin Wright. Their daughter Dylan Frances was born on the 13th of April 1991, and their son Hopper Jack on the 6th of August 1993. During a separation in 1995, Penn spotted the singer Jewel performing on Late Night with Conan O'Brien. He invited her to write a song for The Crossing Guard and followed her on tour. He reconciled with Wright, and they married on the 27th of April 1996. They filed for divorce in December 2007 and reconciled several months later. After another legal separation filing in April 2009, which was withdrawn in May, Wright filed for divorce on the 12th of August 2009. It was finalized on the 22nd of July 2010.
In December 2013, Penn began dating the South African actress Charlize Theron. Their relationship ended in June 2015. Despite reports that they were engaged, Theron said they never were. In 2016 he began a relationship with the Australian-American actress Leila George. They married on the 30th of July 2020, and the divorce was finalized on the 22nd of April 2022. In June 2023, he began a relationship with Olga Korotyayeva, from Ukraine. In a June 2024 interview he confirmed he was single again.
In October 1985, Penn pleaded no contest to charges that he assaulted two journalists who tried to photograph him and Madonna in Nashville. He was fined $50 on each of two misdemeanor counts. In April 1987, Penn violated probation by punching a film extra, Jeffrey Klein, on the set of Colors. He was sentenced to 60 days in jail for this assault and for reckless driving, and he served 33 days. By his own account, the jail also held the serial killer Richard Ramirez, who wrote to him. Penn wrote back that he felt no kinship with a fellow inmate. In May 2010, Penn pleaded no contest to a misdemeanor charge from a clash with the photographer Frank Mateljan. He was sentenced to 300 hours of community service and 36 hours of anger management counseling.
In 2015, director Lee Daniels referred to Penn's rumored history of domestic violence while defending Terrence Howard. Penn filed a $10 million defamation suit, saying he had never been arrested for or charged with domestic violence. He dropped the suit in May 2016, after Daniels retracted his statement and apologized.
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Common questions
Who is Sean Penn?
Sean Penn is an American actor and filmmaker, born in Santa Monica, California, on the 17th of August 1960. He is known for intense leading roles and has won three Academy Awards.
How many Academy Awards has Sean Penn won?
Sean Penn has won three Academy Awards. He won Best Actor for Mystic River and for Milk, and Best Supporting Actor for One Battle After Another.
What was Sean Penn's first feature film?
Sean Penn made his feature film debut in the drama Taps in 1981. He played a cadet at a military high school.
Which films has Sean Penn directed?
Sean Penn directed The Indian Runner (1991), The Crossing Guard (1995), The Pledge (2001) and Into the Wild (2007). He later directed The Last Face (2016), Flag Day (2021) and the documentary Superpower (2023).
What is Sean Penn's connection to Ukraine?
Sean Penn has visited Ukraine five times, including a trip in March 2026 when he skipped the Academy Awards ceremony. He directed the documentary Superpower about president Volodymyr Zelenskyy, who awarded him the Ukrainian Order of Merit.
What is the J/P Haitian Relief Organization founded by Sean Penn?
Sean Penn founded the J/P Haitian Relief Organization after the 2010 Haiti earthquake. It operated a tent camp for 55,000 people, and Haitian president Michel Martelly named Penn Ambassador-at-Large for Haiti on the 31st of January 2012.
Why did Sean Penn interview El Chapo?
Sean Penn and the actress Kate del Castillo secretly interviewed Sinaloa Cartel boss Joaquín "El Chapo" Guzmán before his capture. Rolling Stone reported the meeting on the 9th of January 2016, and del Castillo had brokered it while discussing a possible biographical film.
All sources
205 references cited across the entry
- 1Sean PennA&E Television Networks
- 2Leak sinks Penn's rescue mission hopesSeptember 7, 2005
- 3News'He was born for this moment': Sean Penn on his film with ZelenskyDavid Smith — September 18, 2023
- 4BookCulture Wars: An Encyclopedia of Issues, Viewpoints, and VoicesM.E. Sharpe — 2010
- 5Sean Penn Is Esquire's March Cover StarAlex Bilmes — February 16, 2015
- 6Actor Chris Penn found dead at residenceTribune — January 24, 2006
- 7Hollywood star Sean Penn's grandfather came from which town in Lithuania?The Lithuanian Tribute — February 19, 2012
- 8NewsSpectatorNaomi Pfefferman — October 16, 1997
- 11BookSean Penn: His Life and TimesCanongate Books — 2004
- 12According to Penn's mother, his father may have had distant Sephardic Jewish ancestry, as his family's surname was originally "Piñón".
- 13NewsSean Penn, an optimist who tries to save the worldLeah Garchik — January 21, 2016
- 14NewsDon't Get Him StartedRachel Abramowitz — January 6, 2002
- 15Stated on Inside the Actors Studio, 1999
- 16'Little House on the Prairie': The Uncredited Role Sean Penn Played in the SeriesEvan Reier — February 20, 2021
- 19'When Sean's having fun, it's hard to imagine having more fun'Richard T. Kelly — April 8, 2005
- 21NewsReview/Film; Resolving the Painful Love Between 2 BrothersJanet Maslin — September 20, 1991
- 22Carlito's Way (1993)July 26, 2023
- 23Carlito's WayNovember 8, 1993
- 26NewsFILM REVIEW;From Sean Penn, a Raw Style and a VisionJanet Maslin — November 15, 1995
- 27From 'Dead Man Walking' to 'Milk': 9 Essential Sean Penn PerformancesFebruary 26, 2022
- 29The 68th Academy AwardsOctober 5, 2014
- 30MagazineShe's So Lovely
- 34NewsHurlyburlyPeter Bradshaw — April 7, 2000
- 35The Play Is Not the Thing: Anthony Drazan directs "Hurlyburly"January 4, 1999
- 37MagazineSean Penn discusses Woody Allen's Oscar-worthy directing styleJosh Wolk Wolk — February 17, 2000
- 39The 72nd Academy AwardsApril 22, 2015
- 42Magazine33 stars you forgot were on Friends
- 43'I Am Sam' Director Jessie Nelson Wouldn't Make Her Movie the Same Way NowMark Peikert — December 31, 2021
- 44MagazineSean Penn had a memorable 2004 Oscars momentEW Staff — March 1, 2004
- 45Mystic RiverMay 23, 2003
- 48NewsBafta awards 2004: The winnersFebruary 15, 2004
- 49Press releaseAcademy Invites 127 to MembershipAcademy of Motion Picture Arts and Sciences — June 28, 2004
- 51MagazineInto the Wild
- 52DGA Award NomineesJanuary 23, 2008
- 53Milk Review: 2008 MovieNovember 2, 2008
- 54NewsSpirit Award nominees announcedErin Maxwell — work — December 3, 2008
- 56Sean Penn wins best actor Oscar for "Milk"February 23, 2009
- 58NewsFair Game – reviewPhilip French — March 13, 2011
- 59'Tree of Life' wins Palme d'OrMay 22, 2011
- 61'This Must Be the Place': What the Critics Are SayingNovember 2012
- 63NewsSean Penn, Satirist, Swings at America in a Wild Debut NovelJeff Giles — March 27, 2018
- 64MagazineSean Penn: Why I Had to Write 'Bob Honey Who Just Do Stuff'April 4, 2018
- 65NewsSean Penn pivots from actor to novelist at La Jolla readingApril 7, 2018
- 67MagazineSean Penn on Quitting the Movie Business, His New First Novel, and #MeTooApril 6, 2018
- 69The First ReviewSeptember 12, 2018
- 71'The First' Canceled at Hulu After One SeasonJanuary 19, 2019
- 76This Is Us, Succession, Severance, Ted Lasso Lead 2022 HCA TV NominationsDenise Petski — July 7, 2022
- 77News'Superpower' Review: Sean Penn Chronicles the War in UkraineBen Kenigsberg — September 18, 2023
- 82One Battle After AnotherPaul Thomas Anderson — Ghoulardi Film Company, Warner Bros. — 2025-09-26
- 83Interview"На вході — Шон Пенн, на виході — українські таланти". Олег Кохан та Андрій Лідаговський про "Війну очима тварин"Oleg Kokhan et al. — Suspilne — November 18, 2025
- 86NewsMadonna Comes Forward About Sean Penn's Alleged Abuse: 'Sean Has Never Struck Me'Marlow Stern — December 19, 2015
- 87MagazineMadonna and Sean Penn: Justifying their loveBob Cannon — August 14, 1992
- 88NewsMadonna's love historyOctober 15, 2008
- 89Sean Penn got into another fight with a photographer...August 30, 1986
- 90Everyone Said It Wouldn't Last...Joanne Kaufman — December 14, 1987
- 91Madonna Withdraws Assault Complaint Against Sean PennJeff Wilson — January 11, 1989
- 92NewsThe Incident Behind Those Sean Penn Domestic Abuse AllegationsSeptember 22, 2015
- 93NewsA Marriage Filled With AbuseChristopher Andersen — November 6, 1991
- 94NewsMadonna Says Sean Penn 'Never Struck Me', Backs Ex In $10M Lee Daniels Defamation SuitDominic Patten — December 17, 2015
- 95Cradle WatchAleene MacMinn — April 17, 1991
- 96NewsPassagesMaria Speidel — August 23, 1993
- 97Jewel Reveals Pre-Fame Relationship With Sean Penn: 'I Liked His Mind'Sophie Schillaci — September 23, 2015
- 98Sean Penn and Robin Wright Penn DivorcingNicholas White — December 27, 2007
- 99Sean Penn Files for Legal SeparationMarisa Laudadio et al. — April 29, 2009
- 100NewsSean Penn, wife Robin end divorce proceedingPatricia Reaney — April 9, 2008
- 101NewsSean Penn withdraws separation filingMay 21, 2009
- 102Robin Wright Penn Files for DivorceKen Lee — August 18, 2009
- 103Robin Wright Penn Relishes Her New IndependenceStephen M. Silverman — August 17, 2009
- 104Sean Penn and Robin Wright Finalize Their DivorceEunice Oh — August 4, 2010
- 105'The Last Face' and the tale of Charlize Theron and Sean PennBrooke Metz — July 27, 2017
- 106MagazineCharlize Theron and Sean Penn Have Reportedly Ended Their EngagementJulie Miller — June 17, 2015
- 107Charlize Theron Denies She Was Engaged to Sean Penn: 'I Was Never Going to Marry Him'Alexia Fernández — June 22, 2020
- 108MagazineSean Penn Sweetly Supports Girlfriend Leila George at Her Australian Wildfire Relief Zoo EventAle Russian et al. — March 9, 2020
- 109Sean Penn, 59, Leila George, 28, get married in secret 'COVID wedding'Naledi Ushe — Fox News — August 4, 2020
- 110Sean Penn's Wife Actress Leila George Files for Divorce After 1 Year of MarriageKatie Campione — October 15, 2021
- 113NewsOpinion Sean Penn, Rebel With Many Causes (Published 2024)2024-06-22
- 114Actor Pleads No Contest, Fined On Assault ChargesTom Gillem — October 17, 1985
- 115Actor Sean Penn accused of assaulting journalistJanuary 17, 1986
- 116Actor Sean Penn was charged with battery Friday for...Michael Harris — July 18, 1986
- 117Penn Pleads Not Guilty to Battery ChargeOctober 29, 1986
- 118Arrest Warrant Issued For Sean PennApril 25, 1987
- 119NewsActor Sean Penn Gets 60 Days in JailLois Timnick — June 24, 1987
- 120Ciccone, Christopher (2008). Life with My Sister Madonna, Simon & Schuster, pp. 144–50; .
- 121NewsSean Penn's unlikely pen pal: 'Night Stalker' Richard RamirezShelby Grad — March 10, 2015
- 122Sean Penn pleads to paparazzo kickAlan Duke — CNN — May 12, 2010
- 123NewsSean Penn sent to anger management after paparazzi clashMay 12, 2010
- 124'Empire's' 'Batshit Crazy' Behind-the-Scenes Drama: On the Set of TV's Hottest ShowLacey Rose — September 16, 2015
- 125Sean Penn Files $10 Million Defamation Lawsuit Against 'Empire' Co-Creator Lee DanielsEriq Gardner — September 22, 2015
- 126Sean Penn Wins Apology from Lee Daniels in Defamation SettlementEriq Gardner — May 4, 2016
- 127Sean Penn: Hollywood hellraiser turned activistBBC — January 10, 2016
- 129Letter by Sean PennSean Penn — DrudgeReport Archives — October 8, 2004
- 130NewsChallenger lashes out at Doolittle, calls him 'coward'Associated Press et al. — August 14, 2016
- 132Sean Penn, Val Kilmer, Tom Morello, Cindy Sheehan at Nader/Gonzalez Super Rally in Denver — Ralph Nader for President in 2008Votenader.org — August 19, 2008
- 133NewsSean Penn Interviews Raúl CastroMarc Lacey — November 26, 2008
- 134NewsConan O'Brien, Sean Penn discuss cancel culture calling it 'very Soviet' and 'ludicrous'Tyler McCarthy — July 7, 2021
- 135NewsSean Penn plays politicsScott Bowles — September 18, 2006
- 136Sean Penn Letter to Washington PostNovember 24, 2002
- 137Rees, Paul: 'Listen very carefully, I will say this only once', Q, May 2003, pp84-92
- 138NewsSean Penn: Mr CongenialityRavi Somaiya — October 14, 2007
- 139NewsSean Penn Praised by Venezuela's ChavezIan James — August 2, 2007
- 140Sean Penn Unloads on Pres. BushFox News — March 27, 2007
- 141Stephen Colbert vs Sean PennMarch 27, 2007
- 142An Open Letter to the President...Four and a Half Years LaterSean Penn — March 24, 2007
- 144Penn's rescue attempt springs a leakSeptember 5, 2005
- 145NewsMountain of SnakesSean Penn — November 30, 2008
- 146Sean Penn: It's time to seize opportunities in HaitiThe World Bank — May 3, 2013
- 147Haitian Relief OrganizationJphro.org
- 148NewsThe Accidental ActivistZoe Heller — March 25, 2011
- 149NewsHaiti names Sean Penn 'ambassador at large'CBS News — January 31, 2012
- 150Sean Penn Talks Haiti, Humanitarianism and HollywoodLaura Schreffler — November 3, 2016
- 151Sean Penn Oscar SpeechMahalo.com — February 22, 2009
- 152NewsSean and Dylan Penn on Flag Day: 'It did feel like going through therapy'James Mottram — January 28, 2022
- 153NewsHollywood visitor: Sean Penn comes to BadinMarch 24, 2012
- 154NewsSean Penn comes to PakistanJewishJournal.com — March 24, 2012
- 155NewsA touch of inspiration runs both ways as Sean Penn visits shrine and Edhi homeMarch 25, 2012
- 156NewsActor Sean Penn visits Edhi Centre, KarachiAPP — March 25, 2012
- 158Somebody Call Sean PennLinda Burstyn — Vox Media LLC.
- 159Sean Penn wants to 'save lives' with free COVID-19 testingMarcela Isaza — April 11, 2020
- 160NewsSean Penn the Focus of N.L.R.B. Amid Comments on Hours and Food at Vaccine SiteColin Moynihan — October 28, 2021
- 161NewsExclusive: Venezuela ships fuel to war-torn SyriaFebruary 16, 2012
- 162NewsSean Penn: Journalists who call Hugo Chávez a dictator should be jailedRory Carroll — March 11, 2010
- 163NewsSean Penn Wants Reporters Jailed for Calling Chavez 'Dictator'April 11, 2016
- 164NewsSean Penn Wants Me Thrown In JailMichael Moynihan — March 9, 2010
- 165NewsLiberal Fascism Alert: Sean Penn EditionKevin D. Williamson — March 9, 2010
- 166Hugo Chávez's death draws sympathy, angerCNN — March 6, 2013
- 167NewsDangers of the PennRoger Cohen — January 4, 2009
- 168News'Milk' star Sean Penn: Pal of anti-gay dictators?Patrick Goldstein — December 11, 2008
- 169NewsA Friend to Gays and Antigay Dictators AlikeJames Kirchick — December 9, 2008
- 170NewsSean Penn, journalistMichael Weiss — December 3, 2007
- 171Open Letter to Sean Penn: Actress Confronts Actor On Hugo ChavezJon Bershad — Mediaite.com — March 29, 2010
- 173NewsSean Penn Met With 'El Chapo' for Interview in His Hide-OutRavi Somaiya — January 9, 2016
- 174'El Chapo' Guzmán secretly met Sean Penn in MexicoCNN — January 10, 2016
- 175News"Ola ermoza"…Joaquín López-Dóriga
- 176NewsEl Chapo: Who is Kate del Castillo?Katy Watson — January 11, 2016
- 177Texts Purportedly Reveal El Chapo's Eagerness to Meet Actress Kate del CastilloNBC News — January 13, 2016
- 179NewsPenn won't face US charges over El Chapo interviewJanuary 10, 2016
- 180News'Hermosa', el nombre clave de KateCarlos Loret de Moda — December 1, 2016
- 181NewsKate del Castillo Describes Her and Sean Penn's Meeting With 'El Chapo'19 March 2016
- 182NewsKate del Castillo califica de "escoria" a Sean Penn y asegura que la usó de "carnada" en su encuentro con 'El Chapo'Ana Paula Vázquez — 2 October 2025
- 183NewsArmenians are being slaughtered by Trump pal Erdogan – Sean PennOctober 24, 2020
- 184Sean Penn filming documentary on the ground in UkraineSarah Sicard — February 24, 2022
- 185Sean Penn In Ukraine: Putin Has Made a 'Horrible Mistake', Urges U.S. to FightJamie Burton — February 24, 2022
- 186Sean Penn walked to Polish border to leave UkraineLisa Respers France — CNN — March 4, 2022
- 187Russia sanctions Ben Stiller and Sean Penn over Ukraine supportSeptember 6, 2022
- 188Sean Penn loans his Oscar to Ukraine's president ZelenskiyAndrew Pulver — November 9, 2022
- 190Falklands dispute: Argentine union to boycott UK shipsBBC — February 14, 2012
- 191NewsSean Penn backs Argentina over Falkland IslandsFebruary 14, 2012
- 192News'The world can't tolerate anymore ridiculous colonialism', Sean Penn says after meeting CFKFebruary 15, 2012
- 193NewsSean Penn should return his Malibu estate to the MexicansTim Stanley — February 15, 2012
- 194NewsSean Penn's Argentina Falklands support angers Simon WestonFebruary 16, 2012
- 195NewsSean Penn: Prince William is provoking ArgentinaFebruary 16, 2012
- 196MagazineSEAN PENN'S FALKLANDS WARLauren Collins — February 15, 2012
- 197NewsSean Penn hits out at Prince William's Falklands postingAlexandra Topping, Alexandra — February 15, 2012
- 198NewsSean Penn: The Malvinas/Falklands – diplomacy interruptedSean Penn — February 23, 2012
- 199NewsSean Penn calls for Britain to negotiate with Argentina over FalklandsNicholas Watt — February 23, 2012
- 200NewsIn pictures: Sean Penn – Oscar winning actor, ex-husband of Madonna and campaignerFebruary 15, 2012
- 201NewsOscar lead actor nomineesSusan King — January 23, 2009
- 202Directors Guild names favorite directors of '07Bob Tourtellotte — January 8, 2008
- 203Cesar Awards: Sean Penn Calls French Film a "Refuge" From HollywoodFebruary 20, 2015
- 204BookBob Honey Who Just Do Stuff: A NovelSean Penn — Atria Books — 2018
- 205BookBob Honey Sings Jimmy Crack Corn: A NovelSean Penn — Rare Bird Books — 2019