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Sean Penn was born into a Hollywood family in Santa Monica, California, back in 1960: Father Leo Penn was an actor and director and mother Eileen was an actress. It was no surprise when Sean made his TV debut at 14 as an extra on "Little House on the Prairie" in 1974. He's seen here six years later early in 1980.
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Sean Penn made his big-screen debut in 1981's "Taps." He starred in the film alongside Tom Cruise (in his second film role ever), George C. Scott and Timothy Hutton (seen here) as a high school military cadet. But the movie that would turn Sean into a bona fide movie star would come out the following year…
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"Fast Times at Ridgemont High" hit theaters in 1982 and saw Sean Penn playing the iconic character of Jeff Spicoli. The coming-of-age movie written by Cameron Crowe and directed by Amy Heckerling also starred Jennifer Jason Leigh, Judge Reinhold and Phoebe Cates and featured appearances by future big names like Nicolas Cage and Forest Whitaker.
Sean Penn followed "Fast Times at Ridgemont High" with another teen-centered film, 1983's "Bad Boys" — a coming-of-age drama set in a juvenile detention center — opposite Esai Morales (seen here). The movie was a hit with critics, with Sean's performance in particular garnering great reviews.
"Racing With the Moon" paired Sean Penn with Nicolas Cage once again; the two actors starred alongside Elizabeth McGovern in the 1984 drama. Sean went on to propose to Elizabeth after they struck up a relationship on set. But that romance was short lived…
1985 saw Sean Penn step into a spy drama based on a true story. He took on the role of Andrew Daulton Lee in "The Falcon and the Snowman" (opposite Timothy Hutton, seen here) — a man accused of selling U.S. secrets to the Soviet Union. The film received rave reviews and led to an unlikely friendship between Sean and the man he was playing. Once Andrew's parole was up in the '90s, Sean ended up hiring him as his personal assistant.
Cue wedding bells! After his split from Elizabeth McGovern, Sean Penn met singer Madonna in February 1985. The two were married by that August. They're seen here at a Los Angeles screening of his film "At Close Range" in 1986.
"At Close Range" saw Sean Penn play another real-life criminal, this time Brad Whitewood Jr., a member of a Pennsylvania crime family in the '60s and '70s. The 1986 film included music from Sean's then-wife, Madonna — the track "Live to Tell."
Now a certified Hollywood power couple, Sean Penn and Madonna took their union to the big screen for "Shanghai Surprise" in 1986. Despite their star power, the film was a bomb both at the box office and with critics.
Sean Penn joined wife Madonna at her 31st birthday party in Los Angeles in the summer of 1987. But by the end of the year, it appeared things were over. The pop superstar filed for divorce that December, though she later withdrew the papers. Two years later, however, the split was official — Madonna filed for divorce, for good this time, in January 1989.
Sean Penn moved on pretty quickly. After ending his first marriage to Madonna, he started dating Robin Wright after the two met on the set of 1990's "State of Grace." They're seen here at the film's New York City premiere in September 1990.
Baby makes three! Sean Penn and Robin Wright welcomed their first child, daughter Dylan Penn, in April 1991. She's seen here with her proud parents at their Malibu home later that year. Son Hopper would arrive two years later in August 1993.
1991's "The Indian Runner" marked Sean Penn's directorial debut. The crime drama starring David Morse, Viggo Mortensen and Patricia Arquette would be the first of five films Sean helmed.
Sean Penn starred opposite Al Pacino in "Carlito's Way" in 1993. Even though the crime film only found moderate success with critics and audiences, Sean's work in the project earned him a Golden Globe nomination.
Sean Penn accompanied girlfriend Robin Wright to the Los Angeles premiere of her blockbuster film "Forrest Gump" in June 1994, but their roller coaster relationship imploded the following year and they split. However, it wouldn't be the end of the duo.
The next romantic partner for Sean Penn was a surprising one — singer Jewel, who was 14 years his junior. The actor reportedly went on tour with the singer, who also wrote a song for his 1995 film "The Crossing Guard." (The couple are seen here together in 2017).
Sean Penn collected his first Academy Award nomination in 1996 thanks to his work in "Dead Man Walking." The 1995 drama saw him star as a prisoner on death row alongside Susan Sarandon, who won a best actress Oscar for her performance as the nun who helps him appeal his case.
Back on! Sean Penn and Robin Wright not only got back together in 1996 — they married. The following year, the couple starred in a film together, "She's So Lovely," opposite John Travolta. Sean's portrayal of Eddie Quinn earned him the best actor award at the Cannes Film Festival that year.
1998's "Hurlyburly" saw Sean Penn play another character named Eddie! And again, he took home an award thanks to his performance. The film, which was based on a play from the '80s by the same name, helped Sean win the Volpi Cup at that year's Venice Film Festival.
His performance as a jazz guitarist in "Sweet and Lowdown" in 1999 earned Sean Penn another Academy Award nomination. The Woody Allen film was a hit with critics and earned Sean's co-star Samantha Morton a nomination as well.
2001's "I Am Sam" starred Sean Penn as a devoted dad with intellectual disabilities who's doing his best to raise his bright, intelligent daughter — played by a young Dakota Fanning in her breakout role — after her mother abandons them. It earned him his third Academy Award nomination.
When it came time to attend the premiere of "I Am Sam" in December 2001, Sean Penn made it a family affair. Son Hopper, daughter Dylan and wife Robin Wright accompanied him to the event.
Sean Penn's affinity for crime dramas continued in 2003 when he starred in "21 Grams" alongside Naomi Watts, Danny Huston and Benicio Del Toro. It helped earn him a BAFTA nomination for best actor and take home the Volpi Cup at the Venice Film Festival that year.
2004 saw Sean Penn win his very first Academy Award! The actor took home a best actor Oscar for his work in 2003's "Mystic River." Coincidentally, he won alongside future ex-girlfriend Charlize Theron, who was named best actress for her performance in "Monster" that year.
Sean Penn earned the Christopher Reeve First Amendment Award from the Creative Coalition in December 2006, an honor given to him because of his commitment to free speech.
"Into the Wild" hit theaters in September 2007. Sean Penn directed the drama, which starred Emile Hirsch and featured a young Kristen Stewart. The film was critically acclaimed and picked up two Golden Globe nominations, two Academy Award nominations and a best director nod for Sean at the Directors Guild of America Awards.
In 2007, Sean Penn and Robin Wright's relationship got messy. They filed for divorce in December 2007 but eventually withdrew the papers a few months later in 2008. They're seen here, back on, at the New York City premiere of "What Just Happened" that October.
When Sean Penn won a best actor Academy Award for his performance in "Milk" in 2009 — his second Oscar — he used the moment to deliver a powerful acceptance speech in which he voiced his support for same-sex marriage. "We've got to have equal rights for everyone," he told the audience.
Robin Wright was by Sean Penn's side at the Academy Awards in February 2009. By April, their two-decade-long romance was in tatters again. Sean filed for legal separation then withdrew the case when they reconciled that May. However, by August, Robin had filed for divorce, and this time, it stuck: The split was finalized the following year.
Activism became an even bigger part of Sean Penn's life following the implosion of his marriage. In 2010, after a massive earthquake in Haiti, he founded the J/P Haitian Relief Organization, which did incredible work aiding displaced Haitians and people in crisis, and Sean was incredibly hands-on. The nonprofit was later renamed CORE, which stands for Community Organized Relief Effort.
Sean Penn struck up a relationship with another beautiful and talented star in 2013 — Charlize Theron, who's 15 years his junior. They're seen here at the Met Gala in 2014.
A loyal guy! Sean Penn showed up at former love Madonna's "Secret Project Revolution" film screening in 2013, showing that the two had formed a friendship following their divorce nearly 25 years earlier.
But will these two be friendly exes? After two years of dating, Sean Penn and Charlize Theron (who later denied reports they were engaged) called it quits in 2015. They're seen here at the Cannes Film Festival premiere of her film "Mad Max: Fury Road" in May that year. The film they made together, the critically panned "The Last Face" — Sean directed, Charlize starred — came out post-split in 2016.
The rumor mill started back up again in 2015, linking Sean Penn to actress Minka Kelly (who's 20 years his junior). The two faced romance speculation until 2016, though they never confirmed a relationship. They're seen here at an event in Los Angeles in April 2016.
The fifth film directed by Sean Penn — "The Last Face" — debuted at the 69th Annual Cannes Film Festival in May 2016. He brought along son Hopper and daughter Dylan to celebrate.
In 2016, Sean Penn started dating actress Leila George, who's more than 30 years his junior and happens to be the daughter of fellow actors Vincent D'Onofrio and Greta Scacchi. Sean and Leila are seen here at an event that October.
Sean Penn added another accomplishment to his resume in 2018 — author. That March, he published the novel "Bob Honey Who Just Do Stuff," a satirical fiction tale he said is based on modern American culture.
In October 2018, Sean Penn attended the GO Campaign Gala with daughter Dylan Penn, who's been carving out a career as an actress and model.
Sean Penn and Leila George had what he called a "COVID wedding" in July 2020. They couple tied the knot with "a county commissioner [presiding] on Zoom," Sean told late night host Seth Meyers days later. "We were at the house, my two children [with ex Robin Wright] and her brother, and we did it that way." Sean and Leila are seen here at an Australian wildfire relief fundraiser three months before they said "I do."