Sean Penn
American actor and filmmaker
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| 2023 | Penn directed his first documentary 'Superpower', profiling Ukrainian President Volodymyr Zelenskyy, which premiered at the Berlin International Film Festival. |
| 2023 | Penn starred as a cab driver in Christy Hall's directorial debut 'Daddio', acting opposite Dakota Johnson. |
| June 2023 | Began relationship with Ukrainian Olga Korotyayeva |
| 2022 | Penn publicly commented on masculinity, expressing views that men in American culture have become 'wildly feminised' and criticizing what he perceived as a trend of men changing their gender expression. |
| 2022 | Plays John N. Mitchell in the Starz political thriller miniseries Gaslit. |
| November 2022 | In Kyiv, Penn lent an Oscar statuette to President Zelenskyy and was awarded the Ukrainian Order of Merit. |
| April 22 2022 | Divorce from Leila George finalized |
| February 25 2022 | Penn visited Ukraine to film a documentary about the Russian invasion, attended press briefings in Kyiv, met with officials, and publicly supported Ukraine, stating 'If we allow it to fight alone, our soul as America is lost.' |
| 2021 | Penn publicly denounced cancel culture, describing it as 'ludicrous' and expressing his views on contemporary social discourse. |
| 2021 | Penn directed the crime/drama film 'Flag Day' with Dylan Penn and Josh Brolin. |
| 2021 | Penn portrayed Jack Holden in Paul Thomas Anderson's comedy-drama 'Licorice Pizza'. |
| October 15 2021 | Leila George filed for divorce |
| 2020 | Penn played himself in a cameo role in the 'Curb Your Enthusiasm' season 10 episode 'The Spite Store'. |
| July 30 2020 | Married Leila George |
| 2019 | Released his second book 'Bob Honey Sings Jimmy Crack Corn' with Rare Bird Books, continuing his exploration of writing fiction. |
| January 18 2019 | Hulu canceled 'The First' after one season. |
| 2018 | Portrays an astronaut in the Hulu drama series The First. |
| March 2018 | Atria Books published Penn's novel 'Bob Honey Who Just Do Stuff', after which he went on a highly publicized press tour. |
| 2016 | Began relationship with Australian actress Leila George |
| 2016 | Penn directed the drama film 'The Last Face', starring Charlize Theron and Javier Bardem. |
| January 9 2016 | Penn and actress Kate del Castillo conducted a secret interview with Sinaloa Cartel boss Joaquín 'El Chapo' Guzmán prior to his arrest, which was reported by Rolling Stone and criticized by the White House and Mexican authorities. |
| 2015 | Penn starred in the action thriller 'The Gunman', playing Jim Terrier, a sniper on a mercenary assassination team who kills the minister of mines of the Congo. |
| 2015 | Receives an Honorary César Award. |
| June 2015 | Ended relationship with Charlize Theron |
| 2013 | Penn played a role in securing the release of American entrepreneur Jacob Ostreicher from a Bolivian prison and personally nursed him back to health after his release. |
| December 2013 | Began dating actress Charlize Theron |
| March 24 2012 | During his visit to Pakistan, Penn visited Bilquis Edhi Female Child Home, met humanitarian workers Abdul Sattar Edhi and Bilquis Edhi, and laid floral wreaths at the shrine of Abdullah Shah Ghazi. |
| March 23 2012 | Sean Penn visited flood-stricken villages in Karim Bux Jamali, Dargah Shah Gurio, and Peero Lashari in the Badin District of Pakistan, accompanied by U.S. Consul General William J. Martin. He distributed blankets, quilts, kitchen items, and other goods to flood survivors. |
| 2010 | Provides humanitarian aid following the Haiti earthquake. |
| May 2010 | Pleaded no contest to a misdemeanor charge for an altercation with photographer Frank Mateljan in October 2009, sentenced to 300 hours of community service and 36 hours of anger management counseling |
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