Sean Penn, 59, Secretly Marries Actress Leila George, 28, Who Is 31 Years His Junior

That spring; by June 2011, PEOPLE reported they were no longer together. In 1995, Penn saw an early performance by singer-songwriter Jewel on Late Night with Conan O'Brien and reached out to her at her family's home in Alaska to arrange a meeting. The Oscar winner also admitted that he was pretty relieved to have a low-key wedding with George, 28, despite many Hollywood couples who made the decision to postpone their nuptials.

'love those pants'

He explained his relationship with the actress might seem too late, but for him to have met someone who he cares about and is very much passionate about is a happier feeling. It is also very romantic and fulfilling to feel good in a relationship. Though Penn and George have been together since 2016, a friend of the actress told PEOPLE in August, following their nuptials, that the pair had reunited earlier in 2020 after a stretch of being on and off.

After separation with Madonna, Penn married to Robin Wright. Seven years after his divorce from Madonna, Penn and House of Cards star Robin Wright wed in 1996. In early 2014, reports surfaced that Penn was dating a fellow Oscar winner, actress Charlize Theron. They quietly got engaged that December, but by the following June, it was revealed that the couple had ended their relationship. Both Penn and Wright ended their relationships with other people last year. Wright filed for divorce from Clément Giraudet in September, and Penn finalized his divorce from Leila George in April.

Won the Academy Award for Best Actor for his roles in the films Mystic River and Milk . He first earned recognition for his role in the 1982 high school comedy Fast Times at Ridgemont High, then went on to play leading roles in such films as Carlito’s Way , Dead Man Walking , I Am Sam and 21 Grams . His childhood friends included actors Charlie Sheen and Emilio Estevez, whom he created short films with.

El Chapo interview

George was raised by her mother and has three younger half-brothers. The couple were seen passing by a local grocery store after having lunch together. The Mystic River actor wore ripped blue jeans and sneakers with a striped flannel over a black tee. He stepped out of his vehicle with a face mask in his hand and holding Leila’s hand before entering the Pavilions. The insider added that the time self-isolating together during the pandemic helped strengthen their connection.

The same year, he was invited to join the Academy of Motion Picture Arts and Sciences. Next, Penn portrayed governor Willie Stark in an adaptation of Robert Penn Warren's classic 1946 American novel All the King's Men . The film was a critical and commercial failure, named by a 2010 Forbes article as the biggest flop in the last five years. Penn made his feature film directorial debut with The Indian Runner , followed by the drama film The Crossing Guard and the mystery film The Pledge ; all three were critically well received.

Years after the release of "Rebel Heart," Madonna confirmed in 2018 that she was working on new music. A year later, she announced that her 14th studio album would be called "Madame X." The album debuted in June 2019 and immediately topped the Billboard 200 chart, earning Madonna her ninth #1 album. Madonna continued to take up space in the history books with "Celebration," a two-CD set that collects about half of her singles, released in 2009. Charts, earning her the distinction of the female artist with the most #1 albums in the U.K.

Penn appeared in a 1974 episode of the Little House on the Prairie television series as an extra when his father, Leo, directed some of the episodes. Penn launched his film career with the action-drama Taps , where he played a military high school cadet. A year later, he appeared in the hit comedy Fast Times at Ridgemont High , in the role of surfer-stoner Jeff Spicoli; his character helped popularize the word "dude" in popular culture. Next, Penn appeared as Mick O'Brien, a troubled youth, in the drama Bad Boys .

Support for same-sex marriage

The two tied the knot in 1997 and share daughters Sophia, 26, Sistine, 24, and Scarlet, 20. Over the past year, both Penn and Wright split from their former spouses. In April 2022, the "Mystic River" star finalized his divorce from actress Leila George, 30, after one year of marriage.

In protest, Madonna began rebelling against her household's strict rules, wearing tampons, and losing her virginity, among others. A pattern of bucking the norms was established at this young age, which led to more controversial decisions later in life, such as nude photos in Playboy and the publication of her book "Sex." The actor, 59, wed his girlfriend of four years, Australian-American actress Leila George, 28, in a low-key ceremony with close family last week. He confirmed the news on “Late Night with Seth Meyers” with a simple flash of his gold wedding band.

Mexican authorities said they were able to zero in on the drug lord's location through his cell phone and electronic exchanges, although it was unclear whether any of those exchanges were with Penn. It was also unclear whether the actor was facing legal problems for his involvement in the situation. Though he previously claimed he quit acting, Penn returned to the front of the camera in 1993, playing a coke-addled criminal lawyer in Brian De Palma's Carlito's Way, co-starring Al Pacino.