History of Sean Penn in Timeline

Sean Penn is a highly acclaimed American actor and director known for his powerful performances. His illustrious career has earned him two Academy Awards, a Cannes Film Festival Award, a Golden Globe Award, two Volpi Cup Awards, a Screen Actors Guild Award, and numerous nominations, including three BAFTA Awards. In 2015, he received the Honorary César Award.

August 17, 1960: Birth of Sean Penn

Sean Justin Penn was born on August 17, 1960, in Santa Monica, California.

1974: Early Television Appearance

Sean Penn made an early television appearance as an extra in a 1974 episode of "Little House on the Prairie", directed by his father.

1981: Film Debut and Broadway Debut

1981 marked a significant year for Penn as he made both his film debut in "Taps" and his Broadway debut in "Heartland".

1981: Broadway Debut in "Heartland"

Sean Penn made his Broadway debut in the play "Heartland" at the Century Theatre in 1981.

1981: Film Debut in "Taps"

Sean Penn made his feature film debut in the drama "Taps" in 1981.

1982: Breakthrough Role in "Fast Times at Ridgemont High"

Penn gained recognition for his role as Jeff Spicoli in the comedy "Fast Times at Ridgemont High" in 1982.

1982: "Fast Times at Ridgemont High" and Cultural Impact

Penn's role in "Fast Times at Ridgemont High" in 1982 contributed to the popularization of the word "dude" in popular culture.

1983: Broadway Appearance in "Slab Boys"

Penn appeared in the John Byrne play "Slab Boys" on Broadway at the Playhouse Theatre in 1983.

1983: Critical Acclaim and Broadway Return

Penn received critical acclaim for "Bad Boys" in 1983 and returned to Broadway for "Slab Boys" alongside Kevin Bacon and Val Kilmer.

1983: Acclaim for "Bad Boys"

Penn's performance in the drama "Bad Boys" in 1983 earned him critical acclaim and established him as a serious actor.

1984: Engagement and Relationship

Sean Penn was engaged to actress Elizabeth McGovern, his co-star in the film "Racing with the Moon," in 1984. He also had a brief relationship with actress Susan Sarandon.

January 1985: Meeting Madonna

Sean Penn met Madonna on the set of her "Material Girl" music video in January 1985.

June 1985: Assault of Journalists

Sean Penn assaulted two journalists who tried to photograph him and Madonna in Nashville in June 1985.

August 16, 1985: Marriage to Madonna

Sean Penn and Madonna got married on August 16, 1985, which was also Madonna's 27th birthday.

October 1985: Assault Charges

Sean Penn pleaded no contest to assaulting two journalists in Nashville in June 1985 and was fined.

1985: Role in "The Falcon and the Snowman"

Sean Penn starred in "The Falcon and the Snowman" in 1985, portraying Andrew Daulton Lee.

January 1986: Assault Charge in Macau

Sean Penn was charged with assaulting a journalist in Macau who photographed him and Madonna.

June 1986: Assault Charge at Nightclub

Sean Penn was charged with misdemeanor battery for assaulting songwriter David Wolinski at a nightclub in Los Angeles.

1986: "True Blue" Dedication and "Shanghai Surprise" Release

In 1986, Madonna dedicated her third studio album, "True Blue," to Sean Penn. They also both starred in the film "Shanghai Surprise" that year.

1986: Critical Acclaim for "At Close Range"

Penn starred in the drama "At Close Range" in 1986, which garnered critical praise.

1986: Critical Acclaim for "At Close Range" and Acting Hiatus

Penn's performance in "At Close Range" in 1986 earned critical acclaim. He then took a break from acting to focus on directing.

April 1987: Assault and Probation Violation

Sean Penn was arrested for assaulting a film extra on set in April 1987, violating his probation.

June 1987: Jail Sentence

Sean Penn was sentenced to 60 days in jail for assault and reckless driving in June 1987.

December 1987: First Divorce Filing

Madonna filed for divorce from Sean Penn in December 1987, but withdrew the papers two weeks later.

January 1989: Second Divorce Filing

Madonna filed for divorce from Sean Penn again in January 1989.

1989: Appearance in "Casualties of War"

Penn appeared in the war drama "Casualties of War" in 1989.

1989: Relationship with Robin Wright Begins

Sean Penn started dating actress Robin Wright in 1989.

1990: Role in "State of Grace"

Penn starred as Detective Terry Noonan in the neo-noir crime film "State of Grace" in 1990.

April 13, 1991: Birth of Dylan Frances Penn

Sean Penn and Robin Wright's first child, Dylan Frances Penn, was born on April 13, 1991.

1991: Directorial Debut with "The Indian Runner"

Inspired by Bruce Springsteen's song "Highway Patrolman" from the 1982 album "Nebraska", Penn made his directorial debut with "The Indian Runner" in 1991.

August 6, 1993: Birth of Hopper Jack Penn

Sean Penn and Robin Wright's second child, Hopper Jack Penn, was born on August 6, 1993.

1993: Return to Acting in "Carlito's Way" and Music Video Direction

Penn returned to acting with a critically acclaimed role in "Carlito's Way" in 1993. That same year, he also directed music videos for Shania Twain and Lyle Lovett.

1993: Performance in "Carlito's Way"

Sean Penn starred alongside Al Pacino in the crime drama "Carlito's Way" in 1993.

1995: Directing "The Crossing Guard" and Oscar-Winning Performance in "Dead Man Walking"

In 1995, Sean Penn directed the thriller "The Crossing Guard" and won an Academy Award for Best Actor for his role in "Dead Man Walking".

1995: Directing "The Crossing Guard"

Penn directed the indie thriller film "The Crossing Guard" in 1995.

1995: Separation and Brief Relationship with Jewel

Sean Penn and Robin Wright separated in 1995. During that time, Penn had a short relationship with singer-songwriter Jewel after seeing her perform on television.

1995: Oscar Nomination for "Dead Man Walking"

Sean Penn received an Academy Award nomination for Best Actor for his role in the crime drama "Dead Man Walking" in 1995.

1995: First Academy Award Nomination for Sean Penn

Sean Penn's performance in "Dead Man Walking" garnered him his first Academy Award nomination for Best Actor in 1995.

April 27, 1996: Marriage to Robin Wright

Sean Penn and Robin Wright married on April 27, 1996, after reconciling following a separation.

1997: Roles in "She's So Lovely" and "The Game"

Penn appeared in the romantic drama "She's So Lovely" and the mystery thriller "The Game" in 1997.

1997: Cannes Film Festival Award and Notable Roles

Penn won the Best Actor award at the Cannes Film Festival for "She's So Lovely" in 1997. He also starred in "U Turn" and "The Game" that year.

1997: Volpi Cup for "Hurlyburly" and Role in "The Thin Red Line"

Sean Penn won the Volpi Cup for Best Actor at the Venice Film Festival for his role in "Hurlyburly" in 1997, adapted from the 1984 play. He also had a leading role in "The Thin Red Line" that year.

1998: Release of "The Thin Red Line"

"The Thin Red Line", based on James Jones's 1962 novel, was released in 1998, featuring Sean Penn in a significant role.

1998: Hiring Andrew Daulton Lee

After portraying Andrew Daulton Lee in "The Falcon and the Snowman", Penn hired Lee as his personal assistant upon Lee's parole in 1998.

1999: Sean Penn Receives Third Academy Award Nomination

In 1999, Sean Penn's performance in "Sweet and Lowdown" earned him his third Academy Award nomination for Best Actor.

1999: Oscar Nomination for "Sweet and Lowdown"

Penn earned an Academy Award nomination for Best Actor for his performance in the Woody Allen film "Sweet and Lowdown" in 1999.

2000: Acting in Films

In 2000, Sean Penn showcased his acting prowess in two notable films: Julian Schnabel's "Before Night Falls" alongside Javier Bardem and Kathryn Bigelow's thriller "The Weight of Water" with Elizabeth Hurley.

2001: Directing "The Pledge"

Expanding his artistic repertoire, Sean Penn directed the mystery film "The Pledge" in 2001.

2001: Fourth Academy Award Nomination for Sean Penn

Sean Penn received his fourth Academy Award nomination for Best Actor in 2001 for his role in "I Am Sam."

2001: Guest Starring and Critical Acclaim

Sean Penn took on a guest role as Eric in the popular NBC sitcom "Friends" in 2001. The same year, he delivered a powerful performance as a mentally challenged father in "I am Sam," earning him his third Academy Award nomination for Best Actor.

2001: Oscar Nomination for "I Am Sam"

Sean Penn was nominated for an Academy Award for Best Actor for his role in the drama film "I Am Sam" in 2001.

October 18, 2002: Open Letter to President Bush

Sean Penn published an open letter as an advertisement in The Washington Post, urging President George W. Bush to end military actions in Iraq.

December 2002: Madonna's Support for Penn's Activism

Madonna expressed support for Sean Penn's criticism of the Bush administration and his activism regarding the Iraq War in December 2002.

2002: Directing Peter Gabriel's Music Video

Sean Penn further explored his directorial talents in 2002 by helming the music video for Peter Gabriel's song "The Barry Williams Show."

2002: Visit to Iraq

Sean Penn visited Iraq in 2002 to protest against the Bush administration's potential plans for military action.

2003: Award-Winning Performance in "Mystic River"

In 2003, Sean Penn starred in Clint Eastwood's "Mystic River," portraying a grieving father seeking justice. His performance garnered widespread acclaim and earned him numerous accolades, including the Academy Award, Critics' Choice Movie Award, and Golden Globe Award for Best Actor.

2003: Academy Award for "Mystic River"

Sean Penn won his first Academy Award for Best Actor for his performance as a grieving father in "Mystic River" in 2003.

2003: Sean Penn Wins First Academy Award for Best Actor

Sean Penn's performance in "Mystic River" earned him his first Academy Award for Best Actor in 2003.

2004: Portraying Samuel Bicke and Joining the Academy

Sean Penn took on the challenging role of Samuel Bicke, based on the real-life figure who attempted to assassinate President Richard Nixon, in the 2004 film "The Assassination of Richard Nixon." This year also marked his invitation to join the prestigious Academy of Motion Picture Arts and Sciences.

June 10, 2005: Visit to Iran

Sean Penn visited Iran on June 10, 2005, as a journalist for the San Francisco Chronicle and attended Friday prayer at Tehran University.

September 2005: Hurricane Katrina Relief Efforts

In September 2005, Sean Penn traveled to New Orleans to provide aid to victims of Hurricane Katrina, actively participating in rescue efforts.

2005: Humanitarian Work After Hurricane Katrina

Sean Penn engaged in humanitarian work in the aftermath of Hurricane Katrina in 2005.

January 7, 2006: "Out of Iraq Forum"

Sean Penn was a special guest at the "Out of Iraq Forum" in Sacramento, California, advocating for the anti-Iraq War movement.

December 18, 2006: Christopher Reeve First Amendment Award

Sean Penn received the Christopher Reeve First Amendment Award from the Creative Coalition for his commitment to free speech on December 18, 2006.

2006: Starring in "All the King's Men"

In 2006, Sean Penn portrayed Governor Willie Stark in the film adaptation of Robert Penn Warren's novel "All the King's Men." Despite the source material's acclaim, the film faced both critical and commercial disappointment.

2006: Featured in Spike Lee's Documentary "When the Levees Broke"

Sean Penn was interviewed by Spike Lee for his documentary "When the Levees Broke: A Requiem in Four Acts" (2006), which chronicled the aftermath of Hurricane Katrina.

2006: Death of Chris Penn

Sean Penn's younger brother, actor Chris Penn, passed away in 2006.

April 19, 2007: Appearance on The Colbert Report and Criticism of Bush Administration

On April 19, 2007, Sean Penn appeared on The Colbert Report, engaging in a satirical debate with Stephen Colbert about Penn's criticisms of the Bush administration and the Iraq War. Penn's impassioned remarks, including a challenge to those "who bathe in the moisture of your soiled and blood-soaked underwear," reflected his strong anti-war stance.

December 7, 2007: Support for Dennis Kucinich and Continued Criticism of Bush Administration

On December 7, 2007, Sean Penn announced his support for Dennis J. Kucinich in the 2008 U.S. presidential election. He continued his criticism of President George W. Bush's handling of the Iraq War, even questioning the stance of Bush's daughters on the conflict.

December 2007: First Divorce Filing from Wright

Sean Penn and Robin Wright first filed for divorce in December 2007 but reconciled several months later.

2007: Directing "Into the Wild"

Penn directed the biographical adventure drama "Into the Wild" in 2007.

2007: Critical Acclaim for Directing "Into the Wild"

Sean Penn received critical acclaim for his direction of the biographical drama and survival film "Into the Wild" in 2007. His work on the film earned him a nomination for the Directors Guild of America Award for Outstanding Directing.

2007: Sean Penn Earns Directors Guild of America Nomination

Sean Penn's directorial work on "Into the Wild" was recognized with a Directors Guild of America nomination in 2007.

August 2008: Support for Open Debates

Sean Penn showed his support for open debates by attending one of Ralph Nader's "Open the Debates" rallies in August 2008.

October 2008: Visit and Interview in Cuba

Sean Penn traveled to Cuba in October 2008, where he met with and interviewed Cuban president Raúl Castro.

November 2008: Oscar-Winning Performance as Harvey Milk

In November 2008, Sean Penn delivered a critically acclaimed performance as Harvey Milk, the real-life politician and gay rights activist, in Gus Van Sant's biographical drama "Milk." This performance earned him widespread recognition and his second Academy Award for Best Actor, along with a Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Leading Role.

2008: U.S. Presidential Election and Political Activism

In 2008, Sean Penn actively participated in the U.S. presidential election by endorsing and campaigning for Dennis J. Kucinich, reflecting his ongoing engagement in political activism.

2008: Academy Award for "Milk"

Penn won his second Academy Award for Best Actor for his portrayal of Harvey Milk in the biopic "Milk" in 2008.

2008: Second Best Actor Oscar for Sean Penn

Sean Penn received his second Academy Award for Best Actor in 2008 for his portrayal of Harvey Milk in the biopic "Milk."

February 22, 2009: Academy Award for Best Actor and Advocacy for LGBTQ+ Rights

On February 22, 2009, Sean Penn won the Academy Award for Best Actor for his portrayal of Harvey Milk in the film "Milk." During his acceptance speech, he passionately advocated for LGBTQ+ rights, urging for equal rights for all and condemning opposition to same-sex marriage.

April 2009: Penn Files for Legal Separation

Sean Penn filed for legal separation from Robin Wright in April 2009, but they later reconciled.

August 12, 2009: Wright Files for Divorce

Robin Wright filed for divorce from Sean Penn for the second and final time on August 12, 2009.

October 2009: Altercation with Photographer

Sean Penn was involved in an altercation with photographer Frank Mateljan in October 2009.

March 2010: Defense of Hugo Chávez and Criticism of Journalists

In March 2010, Sean Penn defended Venezuelan President Hugo Chávez, going as far as calling for the imprisonment of journalists who labeled Chávez a dictator. This stance drew criticism from those who viewed Chávez's government as authoritarian and oppressive.

May 2010: Plea Deal in Photographer Altercation

Sean Penn pleaded no contest to a misdemeanor charge from an altercation with a photographer that occurred in October 2009.

July 22, 2010: Divorce from Robin Wright

Sean Penn and Robin Wright's divorce was finalized on July 22, 2010.

2010: Founding of J/P Haitian Relief Organization

In 2010, following the devastating earthquake in Haiti, Sean Penn established the J/P Haitian Relief Organization, demonstrating his commitment to humanitarian aid and disaster relief. The organization played a pivotal role in managing a tent camp that housed 55,000 people.

2010: Starring in "Fair Game"

In 2010, Sean Penn starred as Joseph C. Wilson in the film "Fair Game." The film, based on Valerie Plame's memoir, explored the political scandal surrounding the leak of Plame's identity as a CIA agent.

2010: Humanitarian Aid in Haiti

Penn provided humanitarian assistance following the devastating 2010 Haiti earthquake.

2010: Founding of CORE (Community Organized Relief Effort)

Sean Penn founded the nonprofit organization CORE (Community Organized Relief Effort), further solidifying his dedication to humanitarian work. CORE has been actively involved in providing aid in Haiti following the 2010 earthquake and Hurricane Matthew, as well as administering free COVID-19 tests in the United States during the pandemic.

December 2011: Public Dispute with María Conchita Alonso

In December 2011, Sean Penn was involved in a public altercation with actress María Conchita Alonso, his co-star from the film "Colors." The dispute, stemming from their differing political views, particularly regarding Hugo Chávez, escalated into a verbal confrontation at an airport, highlighting the intensity of political disagreements.

2011: Role in "The Tree of Life"

Penn appeared in the experimental drama film "The Tree of Life" in 2011.

2011: Collaboration with Terrence Malick and "This Must Be the Place"

Sean Penn reunited with director Terrence Malick for the drama "The Tree of Life," which won the prestigious Palme d'Or at the 2011 Cannes Film Festival. That same year, he starred opposite Frances McDormand in Paolo Sorrentino's comedy-drama "This Must Be the Place."

January 31, 2012: Appointment as Ambassador-at-Large for Haiti

On January 31, 2012, Sean Penn's humanitarian work in Haiti was formally acknowledged when Haitian President Michel Martelly appointed him as Ambassador-at-Large for Haiti. This unprecedented appointment of a non-Haitian citizen highlighted Penn's significant contributions to the country's recovery efforts.

February 2012: Sean Penn Sparks Controversy with Comments on Falkland Islands Dispute

During a meeting with Argentinian President Cristina Fernández de Kirchner in February 2012, Sean Penn expressed his views on the Falkland Islands dispute, advocating for dialogue and criticizing "ridiculous demonstrations of colonialism." This ignited criticism from British veterans and politicians.

February 2012: British Figures Condemn Sean Penn's Remarks on Falkland Islands

Following his comments on the Falkland Islands dispute in February 2012, Sean Penn faced backlash from prominent British figures. Falklands War veteran Simon Weston deemed his views irrelevant, while MP Patrick Mercer labeled his statement "moronic." The New Yorker compared the criticism to that received by Karl Lagerfeld after his controversial remarks about the UK.

February 2012: Support for Hugo Chávez and the Syrian Government

In February 2012, Sean Penn publicly stood with Venezuelan President Hugo Chávez, expressing support for Chávez's government and its support for the Syrian government led by Bashar al-Assad, despite ongoing human rights concerns in both Venezuela and Syria.

March 23, 2012: Humanitarian Visit to Pakistan

On March 23, 2012, Sean Penn traveled to Pakistan, visiting flood-affected areas in the Badin District. Accompanied by U.S. Consul General William J. Martin, Penn distributed essential relief items to flood survivors, demonstrating his commitment to humanitarian aid beyond Haiti.

March 24, 2012: Visit to Bilquis Edhi Foundation and Tribute to Abdul Sattar Edhi

Continuing his humanitarian trip to Pakistan, Sean Penn visited the Bilquis Edhi Female Child Home on March 24, 2012, where he met with renowned Pakistani humanitarian worker Abdul Sattar Edhi and his wife, Bilquis Edhi. He paid his respects at the shrine of Abdullah Shah Ghazi, further emphasizing his respect for humanitarian work and local culture.

December 2013: Relationship with Charlize Theron

Sean Penn began dating South African actress Charlize Theron in December 2013.

2013: Role in Securing the Release of Jacob Ostreicher

In 2013, Sean Penn was reportedly instrumental in securing the release of American entrepreneur Jacob Ostreicher from a Bolivian prison. Ostreicher credited Penn with not only playing a role in his release but also providing personal care and support during his recovery.

2013: Mourning the Death of Hugo Chávez

Upon the death of Hugo Chávez in 2013, Sean Penn publicly mourned the Venezuelan leader, referring to him as a "friend" and praising Chávez's commitment to the poor. This expression of grief further underscored Penn's controversial alignment with Chávez's political ideology.

June 2015: Breakup with Charlize Theron

Sean Penn and Charlize Theron ended their relationship in June 2015.

July 2015: Contact with El Chapo's Lawyer and Interview Arrangements

In July 2015, following El Chapo's escape from prison, communication between Sean Penn, Kate del Castillo, and El Chapo's lawyer intensified, eventually leading to the arrangement of a secret interview.

September 16, 2015: Lee Daniels' Controversial Statement

Filmmaker Lee Daniels made a controversial statement comparing Terrence Howard's domestic violence issues to Sean Penn's rumored history, leading Penn to file a defamation lawsuit.

2015: Madonna Denies Assault Allegations

In 2015, Madonna publicly denied allegations that Sean Penn had assaulted her during their marriage, calling the claims "completely outrageous, malicious, reckless, and false."

2015: Sean Penn Receives Honorary César Award

In 2015, Sean Penn was honored with the Honorary César Award, a prestigious French film award.

2015: Starring in "The Gunman"

Sean Penn starred in "The Gunman," a French-American action thriller, in 2015. The film featured a notable supporting cast, including Jasmine Trinca, Idris Elba, Ray Winstone, Mark Rylance, and fellow Oscar-winner Javier Bardem.

January 9, 2016: Interview with Joaquín "El Chapo" Guzmán

On January 9, 2016, Rolling Stone published an article by Sean Penn revealing that he and actress Kate del Castillo had conducted a secret interview with fugitive drug lord Joaquín "El Chapo" Guzmán while Guzmán was on the run from authorities.

May 2016: Defamation Lawsuit Dropped

Sean Penn dropped his defamation lawsuit against Lee Daniels in May 2016 after Daniels retracted his statement and apologized.

2016: Directing "The Last Face"

Continuing his directorial pursuits, Sean Penn helmed the drama film "The Last Face" in 2016, which starred Charlize Theron and Javier Bardem.

2016: "The Last Face" Release

Sean Penn directed "The Last Face," starring Charlize Theron, released in 2016. They filmed the movie while they were still a couple.

2016: Relationship with Leila George Begins

Sean Penn started dating actress Leila George, daughter of actors Vincent D’Onofrio and Greta Scacchi, in 2016.

March 2018: Publication of Debut Novel "Bob Honey Who Just Do Stuff"

Sean Penn's debut novel, "Bob Honey Who Just Do Stuff," was published by Atria Books in March 2018, marking his foray into the literary world. Following the book's release, he embarked on a highly publicized press tour.

2018: Television Role in "The First"

Sean Penn starred as an astronaut in the Hulu drama series "The First" in 2018.

2018: Starring in Hulu's "The First"

Sean Penn took on his first leading role in a television series with Hulu's science fiction drama "The First." The series, created by Beau Willimon, featured Penn as Tom Hagerty, an astronaut chosen to be part of the first manned mission to Mars.

January 18, 2019: Hulu Cancels "The First"

Despite positive reviews, Hulu made the decision to cancel the science fiction drama series "The First" after one season. The series, created by Beau Willimon, starred Sean Penn as Tom Hagerty, an astronaut on a mission to Mars.

July 30, 2020: Marriage to Leila George

Sean Penn married Australian actress Leila George on July 30, 2020.

October 2020: Support for Armenia and Criticism of Turkey

In October 2020, Sean Penn expressed his support for Armenia in the Nagorno-Karabakh conflict, condemning Turkey's involvement and criticizing close U.S.-Turkey relations. He linked his stance to the 2020 U.S. presidential election, endorsing Joe Biden.

2020: Cameo Appearance in "Curb Your Enthusiasm"

In 2020, Sean Penn made a cameo appearance as himself in the tenth season of the HBO comedy series "Curb Your Enthusiasm." The episode, titled "The Spite Store," showcased his comedic timing and willingness to embrace lighter roles.

October 15, 2021: George Files for Divorce

Leila George filed for divorce from Sean Penn on October 15, 2021.

October 2021: National Labor Relations Board Complaint against CORE

In October 2021, the National Labor Relations Board (NLRB) filed a complaint against Sean Penn and CORE, alleging violations of U.S. federal labor law. The complaint contended that Penn had "impliedly threatened" employees who raised concerns about working conditions at CORE, including allegations of excessively long workdays.

2021: Criticism of Cancel Culture

In 2021, Sean Penn publicly denounced cancel culture.

2021: Starring in "Licorice Pizza"

In 2021, Sean Penn starred in Paul Thomas Anderson's coming-of-age comedy-drama "Licorice Pizza." Penn portrayed Jack Holden, an actor inspired by William Holden, in the film.

2021: Directing "Flag Day"

Sean Penn directed the crime drama "Flag Day" in 2021, featuring his son, Dylan Penn, and Josh Brolin.

February 25, 2022: Visit to Ukraine and Support for Ukraine Amidst Russian Invasion

In 2022, Sean Penn traveled to Ukraine amidst the Russian invasion to film a documentary about the conflict. He met with Ukrainian officials, journalists, and military personnel to gain firsthand insights into the situation. His vocal support for Ukraine and condemnation of Russia's actions underscored his engagement in global political issues.

April 22, 2022: Divorce from Leila George

Sean Penn and Leila George's divorce was finalized on April 22, 2022.

November 2022: Sean Penn Loans Oscar Statuette to President Zelenskyy

In a gesture of solidarity with Ukraine, Sean Penn loaned his Oscar statuette to President Volodymyr Zelenskyy during a visit to Kyiv in November 2022. Penn stated the award was "a symbolic silly thing" and encouraged Zelenskyy to return it to him upon Ukraine's victory.

2022: Comments on Masculinity and Gender

In 2022, Sean Penn sparked controversy with his comments on masculinity, expressing his view that men in American culture have become "wildly feminized." His remarks, particularly his statement about men surrendering their jeans and putting on skirts, drew criticism and ignited debates about gender roles and stereotypes.

2022: Role in "Gaslit"

Penn portrayed John N. Mitchell in the Starz political thriller miniseries "Gaslit" in 2022.

2022: Starring in Starz's "Gaslit"

Sean Penn returned to television in 2022 with a starring role in the Starz political thriller limited series "Gaslit." He portrayed John N. Mitchell, opposite Julia Roberts as Martha Mitchell. The role required extensive prosthetics to transform Penn's appearance.

June 2023: Relationship with Olga Korotyayeva

Sean Penn began a relationship with Ukrainian Olga Korotyayeva in June 2023.

2023: Directing "Superpower" and Starring in "Daddio"

In 2023, Sean Penn directed his first documentary film, "Superpower," profiling Ukrainian President Volodymyr Zelenskyy. The film premiered at the Berlin International Film Festival. The same year, he starred as a cab driver alongside Dakota Johnson in Christy Hall's directorial debut, "Daddio."