Sean Penn is a highly acclaimed American actor and film director, celebrated for his intense performances and leading roles. He has garnered significant recognition, including two Academy Awards, a Golden Globe Award, and a Screen Actors Guild Award. He has also received nominations for prestigious awards like British Academy Film Awards, an Emmy Award, and a Grammy Award. In 2015, he was honored with an Honorary César Award.
In January 1985, Sean Penn met Madonna on the set of her "Material Girl" music video.
In June 1985, Sean Penn assaulted two journalists when they tried to photograph him and Madonna in Nashville, leading to charges later in October.
On August 16, 1985, Sean Penn married singer-songwriter Madonna on her 27th birthday. Penn turned 25 the next day.
In October 1985, Sean Penn pled no contest to charges that he assaulted two journalists when they tried to photograph him and Madonna in Nashville in June 1985. He was fined $50 on each of two misdemeanor charges of assault and battery.
In January 1986, Sean Penn was charged for allegedly assaulting Leonel Borralho, Macau correspondent for the Hong Kong Standard newspaper, after he photographed Madonna and Penn as they arrived at their hotel room.
In June 1986, Sean Penn was charged with misdemeanor battery for allegedly assaulting songwriter David Wolinski at Helena's nightclub in Los Angeles. Wolinski stated that Penn accused him of trying to kiss Madonna. Penn pled not guilty to the charge.
In April 1987, Sean Penn violated probation and was arrested for punching a film extra, Jeffrey Klein, on set of the movie Colors.
In June 1987, Sean Penn was sentenced to 60 days in jail for assault and reckless driving, stemming from the April incident where he punched a film extra. He served 33 days.
In December 1987, Madonna filed for divorce from Sean Penn, but withdrew the papers two weeks later.
In January 1989, Madonna filed for divorce from Sean Penn again and reportedly withdrew an assault complaint against Penn following an incident at their Malibu, California home during the New Year weekend.
On April 13, 1991, Sean Penn and Robin Wright's first child, a daughter named Dylan Frances, was born.
On August 6, 1993, Sean Penn and Robin Wright's second child, a son named Hopper Jack, was born.
In 1995, Sean Penn was nominated for Academy Award for Best Actor for Dead Man Walking.
On April 27, 1996, Sean Penn and Robin Wright married after reconciling.
In 1999, Sean Penn was nominated for Academy Award for Best Actor for Sweet and Lowdown.
In 2001, Sean Penn was nominated for Academy Award for Best Actor for I Am Sam.
On October 18, 2002, Sean Penn placed a $56,000 advertisement in The Washington Post, publicly asking then President George W. Bush to end military hostilities in Iraq and elsewhere. The advertisement was written as an open letter.
In 2003, Sean Penn won an Academy Award for Best Actor for Mystic River.
On June 10, 2005, Sean Penn visited Iran as a journalist for the San Francisco Chronicle, attending a Friday prayer at Tehran University.
In September 2005, Sean Penn traveled to New Orleans to aid Hurricane Katrina victims, physically involved in rescuing people. There was criticism of a PR stunt as he hired a photographer to come along. He denied such accusations in an article he wrote for HuffPost.
On April 19, 2007, Sean Penn appeared on The Colbert Report and had a "Meta-Free-Phor-All" versus Stephen Colbert that was judged by Robert Pinsky following Penn's criticisms of Bush. Penn won the contest with 10,000,000 points to Colbert's 1.
In December 2007, Sean Penn and Robin Wright filed for divorce but reconciled several months later, requesting a court dismissal of their divorce case.
In 2007, Sean Penn received a Directors Guild of America nomination for directing Into the Wild.
In 2008, Sean Penn won an Academy Award for Best Actor for Milk.
On February 22, 2009, Sean Penn received the Academy Award for Best Actor for his role in the film Milk, and in his acceptance speech, he advocated for equal rights.
In April 2009, Sean Penn filed for legal separation from Robin Wright, only to withdraw the case once again when the couple reconciled in May.
On August 12, 2009, Robin Wright filed for divorce from Sean Penn again.
In October 2009, Sean Penn was involved in an altercation with photographer Frank Mateljan, leading to a misdemeanor charge. He pleaded no contest to the charge in May 2010.
In March 2010, Sean Penn called for the imprisonment of journalists who referred to Venezuelan President Hugo Chávez as a dictator.
In May 2010, Sean Penn pleaded no contest to a misdemeanor charge stemming from an altercation with photographer Frank Mateljan in October 2009. He was sentenced to perform 300 hours of community service and undergo 36 hours of anger management counseling.
On July 22, 2010, the divorce between Sean Penn and Robin Wright was finalized, with a private agreement reached regarding child and spousal support, division of assets, and custody of their son, Hopper.
In 2010, Sean Penn's nonprofit organization Community Organized Relief Effort (CORE) distributed aid in Haiti following the country's earthquake.
In December 2011, Sean Penn and actress María Conchita Alonso had a verbal fight at an airport, during which Penn called her "a pig" and Alonso called Penn a communist.
On January 31, 2012, Sean Penn was designated as Ambassador-at-Large for Haiti by then Haitian president Michel Martelly. He was the first non-Haitian citizen to hold the position in the country's history, because of his advocacy for rescue and aid efforts.
In February 2012, Sean Penn met with the President of Argentina, Cristina Fernández de Kirchner, and commented on the Falkland Islands dispute, advocating for diplomatic dialogue.
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, who deemed Penn's statement "moronic."
On March 23, 2012, Sean Penn, accompanied by US Consul General William J. Martin, visited flood-stricken villages in the Badin District of Pakistan, where he distributed aid to flood survivors.
On March 24, 2012, during his visit to Pakistan, Sean Penn visited Bilquis Edhi Female Child Home and met Pakistani humanitarian worker Abdul Sattar Edhi and his wife Bilquis Edhi, and paid tribute to Abdullah Shah Ghazi.
In December 2013, Sean Penn began dating South African actress Charlize Theron.
In 2013, Sean Penn is believed to have played a role in securing the release of American entrepreneur Jacob Ostreicher from a Bolivian prison, and was credited by Ostreicher for having personally nursed him back to health after his release.
In 2013, upon the death of Hugo Chávez, Sean Penn praised Chávez and his leadership, expressing that the United States had lost a friend and poor people around the world lost a champion.
In June 2015, Sean Penn's relationship with Charlize Theron ended.
Following Joaquín "El Chapo" Guzmán's escape from a Mexican prison in July 2015, communication between actress Kate del Castillo and Guzmán's lawyer increased to discuss producing a biographical film about Guzmán.
In an interview published September 16, 2015, director Lee Daniels responded to criticism about Terrence Howard's continued career by referencing Sean Penn's rumored history of domestic violence.
In 2015, Sean Penn received the Honorary César for lifetime achievement.
On January 9, 2016, Rolling Stone reported that Sean Penn and Kate del Castillo had conducted a secret interview with fugitive Sinaloa Cartel boss Joaquín "El Chapo" Guzmán prior to his arrest.
In May 2016, Sean Penn dropped his $10 million defamation lawsuit against Lee Daniels after Daniels retracted his statement and apologized for referencing Penn's rumored history of domestic violence.
On January 18, 2019, Hulu canceled the science fiction drama series, The First, after only one season. In the series, Sean Penn starred as Tom Hagerty, an astronaut chosen to visit Mars.
On July 30, 2020, Sean Penn married Australian actress Leila George, daughter of actors Vincent D'Onofrio and Greta Scacchi.
On October 15, 2021, Leila George filed for divorce from Sean Penn.
In October 2021, the National Labor Relations Board filed a complaint alleging that Sean Penn and CORE violated US federal labor law, implying threats to employees after complaints about working conditions.
On February 25, 2022, Sean Penn, who was in Ukraine filming a documentary about the Russian invasion, stated that if America allows Ukraine to fight alone, its soul is lost.
On April 22, 2022, Sean Penn's divorce from Leila George was finalized.
In Kyiv in November 2022, Sean Penn lent an Oscar statuette to President Zelenskyy and in turn, Zelensky awarded Penn the Ukrainian Order of Merit.
In 2022, Sean Penn expressed his position on masculinity, saying that men in American culture have become wildly feminised and that men have become quite feminised.
In June 2023, Sean Penn began a relationship with Ukrainian Olga Korotyayeva.
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