History of Sean Penn in Timeline
Sean Penn is a celebrated American actor and filmmaker, recognized for his powerful performances in leading roles. He's garnered significant acclaim, including three Academy Awards, a Golden Globe, and a BAFTA. Penn's contributions extend beyond acting; he received the Honorary César in 2015 and the Bob Hope Humanitarian Award in 2022, highlighting his broader impact.
4 hours ago : Sean Penn attends Thunder vs Lakers NBA Playoffs Game 4 with celebrities.
Sean Penn was spotted at the Thunder vs Lakers NBA Playoffs Game 4, joining other celebrities like Jaafar Jackson at the courtside. The game was a star-studded affair.
1984: Costarred in Racing with the Moon and Engagement to Elizabeth McGovern
In 1984, Sean Penn costarred in 'Racing with the Moon' with Elizabeth McGovern and was engaged to her.
January 1985: Met Madonna
In January 1985, Sean Penn met singer Madonna on the set of her "Material Girl" music video.
June 1985: Assault Charges in Nashville
In June 1985, Sean Penn was involved in an incident in Nashville and was later charged with assault.
August 16, 1985: Married Madonna
On August 16, 1985, Sean Penn and Madonna married on Madonna's 27th birthday.
October 1985: Pled no contest to assault charges
In October 1985, Sean Penn pled no contest to charges of assaulting two journalists in Nashville in June 1985 and was fined $50 on each of two misdemeanor charges.
January 1986: Charged with Assaulting Journalist in Macau
In January 1986, Sean Penn was charged for allegedly assaulting Leonel Borralho, a journalist in Macau, after he photographed Madonna and Penn.
June 1986: Charged with misdemeanor battery for assaulting David Wolinski
In June 1986, Sean Penn was charged with misdemeanor battery for allegedly assaulting songwriter David Wolinski at Helena's nightclub in Los Angeles.
1986: Starred in Shanghai Surprise and Madonna's True Blue dedication
In 1986, Sean Penn and Madonna starred in 'Shanghai Surprise'. Also in 1986, Madonna dedicated her third studio album, 'True Blue', to Penn.
April 1987: Arrested for punching Jeffrey Klein
In April 1987, Sean Penn violated probation and was arrested for punching Jeffrey Klein, a film extra, on the set of the movie Colors.
June 1987: Sentenced to jail for assault and reckless driving
In June 1987, Sean Penn was sentenced to 60 days in jail for assaulting Jeffrey Klein and for reckless driving, serving 33 days.
December 1987: Madonna first files for divorce
In December 1987, Madonna filed for divorce from Sean Penn but later withdrew the papers two weeks later.
January 1989: Madonna files for divorce again
In January 1989, Madonna filed for divorce from Sean Penn for a second time and reportedly withdrew an assault complaint against Penn.
1989: Began dating Robin Wright
In 1989, Sean Penn started dating actress Robin Wright.
April 13, 1991: Birth of daughter Dylan Frances
On April 13, 1991, Sean Penn and Robin Wright's first child, a daughter named Dylan Frances, was born.
August 6, 1993: Birth of son Hopper Jack
On August 6, 1993, Sean Penn and Robin Wright's second child, a son named Hopper Jack, was born.
1995: Separated from Wright, Dated Jewel
In 1995, Sean Penn and Robin Wright separated, and he developed a relationship with Jewel.
1995: Nominated for Academy Award for Dead Man Walking
In 1995, Sean Penn was nominated for the Academy Award for Best Actor for Dead Man Walking.
April 27, 1996: Married Robin Wright
On April 27, 1996, Sean Penn and Robin Wright reconciled and got married.
1999: Nominated for Academy Award for Sweet and Lowdown
In 1999, Sean Penn was nominated for the Academy Award for Best Actor for Sweet and Lowdown.
2001: Nominated for Academy Award for I Am Sam
In 2001, Sean Penn was nominated for the Academy Award for Best Actor for I Am Sam.
October 18, 2002: Published anti-war advertisement
On October 18, 2002, Sean Penn placed a $56,000 advertisement in The Washington Post, asking President George W. Bush to end military hostilities in Iraq.
December 2002: Visited Iraq briefly
In December 2002, Sean Penn visited Iraq briefly after criticizing the Bush administration's policies in an open letter.
2002: Visited Iraq to protest military strike
From December 13-16, 2002, Sean Penn visited Iraq to protest against the Bush administration's plans for a military strike.
2003: Won Academy Award for Mystic River
In 2003, Sean Penn won the Academy Award for Best Actor for Mystic River.
2003: US Military invaded Iraq
In 2003, the US military and the Coalition of the Willing invaded and removed Saddam Hussein from power in Iraq, which was referenced in the 2004 film Team America.
2004: Responded to Team America satire
In 2004, Sean Penn responded to the satirical film 'Team America: World Police' with an angry letter to its creators, Trey Parker and Matt Stone.
June 10, 2005: Visited Iran as a journalist
On June 10, 2005, Sean Penn visited Iran as a journalist for the San Francisco Chronicle and attended Friday prayer at Tehran University.
September 2005: Aided Hurricane Katrina victims
In September 2005, Sean Penn traveled to New Orleans to aid victims of Hurricane Katrina.
January 7, 2006: Special guest at 'Out of Iraq Forum'
On January 7, 2006, Sean Penn joined Norman Solomon and Cindy Sheehan as a special guest at the 'Out of Iraq Forum' in Sacramento, California.
December 18, 2006: Received Christopher Reeve First Amendment Award
On December 18, 2006, Sean Penn received the Christopher Reeve First Amendment Award from the Creative Coalition for his commitment to free speech.
2006: Interviewed for When the Levees Broke
In 2006, Sean Penn was interviewed by Spike Lee for his documentary about Hurricane Katrina, 'When the Levees Broke: A Requiem in Four Acts'.
April 19, 2007: Appeared on The Colbert Report
On April 19, 2007, Sean Penn appeared on 'The Colbert Report' and won a "Meta-Free-Phor-All" against Stephen Colbert following Penn's criticisms of Bush.
December 2007: Filed for Divorce
In December 2007, Sean Penn and Robin Wright filed for divorce but reconciled several months later, requesting a court dismissal of their divorce case.
2007: Directors Guild of America nomination for Into the Wild
In 2007, Sean Penn received a Directors Guild of America nomination for directing Into the Wild.
August 2008: Attended Ralph Nader's 'Open the Debates' rally
In August 2008, Sean Penn attended one of Ralph Nader's 'Open the Debates' super rallies.
October 2008: Visited Cuba and met Raúl Castro
In October 2008, Sean Penn visited Cuba and interviewed then-Cuban president Raúl Castro.
2008: Supported Dennis J. Kucinich
In 2008, Sean Penn supported Dennis J. Kucinich in the US presidential election.
2008: Won Academy Award for Milk
In 2008, Sean Penn won the Academy Award for Best Actor for Milk.
February 22, 2009: Received Academy Award for Best Actor for Milk
On February 22, 2009, Sean Penn won the Academy Award for Best Actor for his role in the movie Milk and used his acceptance speech to advocate for equal rights for gay marriage.
April 2009: Filed for Legal Separation
In April 2009, Sean Penn filed for legal separation from Robin Wright, but withdrew the case in May after reconciliation.
August 12, 2009: Wright Files for Divorce Again
On August 12, 2009, Robin Wright filed for divorce from Sean Penn again.
October 2009: Altercation with photographer Frank Mateljan
In October 2009, Sean Penn was involved in an altercation with photographer Frank Mateljan.
March 2010: Called for the imprisonment of journalists critical of Hugo Chávez
In March 2010, Sean Penn publicly called for the imprisonment of journalists who referred to Venezuelan President Hugo Chávez as a dictator, sparking criticism.
May 2010: Sentenced for altercation with photographer
In May 2010, Sean Penn pleaded no contest to a misdemeanor charge stemming from the October 2009 altercation with photographer Frank Mateljan and was sentenced to community service and anger management counseling.
July 22, 2010: Divorce Finalized
On July 22, 2010, Sean Penn and Robin Wright's divorce was finalized, and they reached a private agreement on child and spousal support, division of assets, and custody of Hopper.
2010: Founder of CORE
In 2010, Sean Penn founded the nonprofit organization Community Organized Relief Effort (CORE).
2010: Founded J/P Haitian Relief Organization
In 2010, following the Haiti earthquake, Sean Penn founded the J/P Haitian Relief Organization to provide aid, despite admitting he had never visited Haiti before and did not speak French or Creole.
December 2011: Verbal fight with Maria Conchita Alonso
In December 2011, Sean Penn and actress María Conchita Alonso engaged in a verbal altercation at an airport, stemming from their differing views on Hugo Chávez.
January 31, 2012: Appointed Ambassador-at-Large for Haiti
On January 31, 2012, Sean Penn was appointed as Ambassador-at-Large for Haiti by then-President Michel Martelly, becoming the first non-Haitian citizen to hold this position.
February 2012: Comments on the Falkland Islands dispute
In February 2012, Sean Penn met with the president of Argentina, Cristina Fernández de Kirchner, in Buenos Aires, and commented on the long-running dispute between Argentina and the United Kingdom over the Falkland Islands, calling for dialogue.
February 2012: Criticism of Penn's comments on the Falklands dispute
In February 2012, Sean Penn's comments on the Falklands dispute were criticized by Falklands War veteran Simon Weston and British Conservative MP Patrick Mercer.
February 2012: Stood beside Hugo Chávez during Syrian civil war
In February 2012, during the Syrian civil war, Sean Penn stood beside Venezuelan President Hugo Chávez as Venezuela supported the Syrian government.
March 23, 2012: Visited flood-stricken villages in Pakistan
On March 23, 2012, Sean Penn, accompanied by the US Consul General William J. Martin, visited villages affected by floods in the Badin District of Pakistan, distributing aid to the survivors.
March 24, 2012: Visited Bilquis Edhi Female Child Home in Pakistan
On March 24, 2012, Sean Penn visited the Bilquis Edhi Female Child Home and met with Abdul Sattar Edhi and his wife Bilquis Edhi. He also laid floral wreaths at the shrine of Abdullah Shah Ghazi.
December 2013: Began Dating Charlize Theron
In December 2013, Sean Penn began dating South African actress Charlize Theron.
2013: Secured release of Jacob Ostreicher
In 2013, Sean Penn played a role in securing the release of American entrepreneur Jacob Ostreicher from a Bolivian prison and helped him recover at his home.
2013: Penn comments on Chávez's death
When Hugo Chávez died in 2013, Sean Penn praised Chávez and criticized the US for losing a friend.
June 2015: Relationship with Charlize Theron Ended
In June 2015, Sean Penn and Charlize Theron's relationship ended.
July 2015: Communication increased with Guzmán after prison escape
In July 2015, following Joaquín "El Chapo" Guzmán's escape from a Mexican prison, communication between actress Kate del Castillo and Guzmán increased, leading to a brokered deal for Sean Penn to interview Guzmán.
September 16, 2015: Lee Daniels references Penn's rumored domestic violence
On September 16, 2015, Lee Daniels referenced Sean Penn's rumored history of domestic violence in response to criticism about Terrence Howard's career.
2015: Madonna denies domestic abuse allegations
In 2015, Madonna denied allegations of domestic abuse during her marriage to Sean Penn, calling them "completely outrageous, malicious, reckless, and false."
2015: Meeting with Guzmán
In 2015, Sean Penn met with Joaquin 'El Chapo' Guzmán.
2015: Received the Honorary César
In 2015, Sean Penn received the Honorary César for lifetime achievement.
January 9, 2016: Rolling Stone reports on Penn's interview with El Chapo
On January 9, 2016, Rolling Stone published an article reporting that Sean Penn and Kate del Castillo had conducted a secret interview with Joaquín "El Chapo" Guzmán prior to his arrest.
May 2016: Penn dropped defamation lawsuit
In May 2016, Sean Penn dropped his defamation lawsuit against Lee Daniels after Daniels retracted his statement and apologized.
2016: Theron starred in The Last Face
In 2016, Charlize Theron starred in Sean Penn's film, 'The Last Face'.
2016: Started relationship with Leila George
In 2016, Sean Penn started a relationship with Australian-American actress Leila George.
2018: Stars in The First
In 2018, Sean Penn took on his first leading role in a television series, portraying astronaut Tom Hagerty in the Hulu science fiction drama series 'The First'.
January 18, 2019: Hulu cancels The First
On January 18, 2019, Hulu canceled the science fiction drama series, 'The First,' after one season. Sean Penn starred in the leading role as Tom Hagerty, an astronaut chosen to visit Mars, in the series created by Beau Willimon.
July 30, 2020: Married Leila George
On July 30, 2020, Sean Penn and Leila George got married.
2020: Cameo in Curb Your Enthusiasm
In 2020, Sean Penn made a cameo appearance as himself in an episode of 'Curb Your Enthusiasm', season 10, titled "The Spite Store".
October 15, 2021: George filed for divorce
On October 15, 2021, Leila George filed for divorce from Sean Penn.
October 2021: NLRB complaint against Penn and CORE
In October 2021, the National Labor Relations Board (NLRB) filed a complaint alleging that Sean Penn and CORE violated US federal labor law by threatening employees who complained about working conditions.
2021: Denounced cancel culture
In 2021, Sean Penn denounced cancel culture, describing it as ludicrous.
2021: Stars in Licorice Pizza
In 2021, Sean Penn portrayed Jack Holden in Paul Thomas Anderson's 'Licorice Pizza'.
February 25, 2022: Penn comments on Russia's invasion
On February 25, 2022, Sean Penn stated that "If we allow it [Ukraine] to fight alone, our soul as America is lost," while filming a documentary in Ukraine about the Russian invasion.
April 22, 2022: Divorce from George finalized
On April 22, 2022, Sean Penn's divorce from Leila George was finalized.
November 2022: Penn lends Oscar statuette to Zelenskyy
In November 2022 in Kyiv, Sean Penn lent his Oscar statuette to President Zelenskyy, who in turn awarded Penn the Ukrainian Order of Merit.
2022: Appears in War Through the Eyes of Animals
In 2022, Sean Penn appeared in the Ukrainian anthology film, 'War Through the Eyes of Animals'.
2022: Expressed position on masculinity
In 2022, Sean Penn expressed his opinion that American men have become feminized, leading to some controversy.
2022: Stars in Gaslit
In 2022, Sean Penn starred in the Starz political thriller limited series 'Gaslit' as John N. Mitchell.
June 2023: Started relationship with Olga Korotyayeva
In June 2023, Sean Penn began a relationship with Ukrainian Olga Korotyayeva.
2023: Directs Superpower and Stars in Daddio
In 2023, Sean Penn directed 'Superpower', his first documentary film, profiling Ukraine's president Volodymyr Zelenskyy, and premiered it at the Berlin International Film Festival. Also in 2023, he starred in 'Daddio' alongside Dakota Johnson.
June 2024: Confirmed he was single again
During a June 2024 interview, Sean Penn confirmed that he was again single.
October 2025: Del Castillo criticizes Penn
In October 2025, Kate del Castillo criticized Sean Penn and accused him of using her as "bait" during their 2015 meeting with El Chapo.
2025: Appears on Everybody's Live with John Mulaney and Stars in One Battle After Another
In 2025, Sean Penn appeared on 'Everybody's Live with John Mulaney' on Netflix alongside Adam Sandler. Also in 2025, he starred in 'One Battle After Another', winning multiple awards for his performance.
2025: Won Academy Award for One Battle After Another
In 2025, Sean Penn received the Academy Award for Best Supporting Actor for his performance in One Battle After Another.
March 2026: Visited Ukraine for the fifth time
In March 2026, Sean Penn visited Ukraine for the fifth time, and received a symbolic Oscar-like statuette made from railway material.
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