Celebrities Who Cheated on Multiple Partners

Celebrity relationships often play out in the public eye, where every twist and turn gets dissected by fans and media alike. Infidelity scandals grab headlines because they involve people we admire from afar, and when those stories involve a pattern across different partnerships, they stick around even longer in our collective memory. These situations remind us that even stars face the same messy human challenges everyone else does.

Over the years, quite a few high-profile figures have faced accusations or admissions of stepping out on more than one significant other. The fallout can range from quick apologies to drawn-out divorces, but the details always spark endless conversations. Let’s dive into some of those stories that have shaped how we view these icons.

15. David Letterman

David Letterman built a legendary career hosting late-night shows where he mixed humor with personal revelations. In 2009, he shocked audiences by confessing on air to sexual relationships with multiple female staff members at his production company. Those encounters happened while he was in a committed long-term partnership with his future wife, Regina Lasko, and he paid the women involved to stay silent about them.

The admission came after a blackmail attempt by a former producer who demanded money to keep the affairs quiet. Letterman detailed how the producer knew about the liaisons and used that knowledge to extort him. He stepped down from his CBS show in 2015 after decades on air, and he married Lasko in a quiet ceremony that same year.

14. Woody Allen

Woody Allen directed and starred in films that explored complex family dynamics and moral gray areas. During his 12-year relationship with actress Mia Farrow, he started a romantic involvement with her adopted daughter, Soon-Yi Previn, who was 21 at the time. That affair, which began around 1991, led to the end of his partnership with Farrow and drew widespread criticism from Farrow and their children.

Allen had two previous marriages before Farrow, both of which ended amid reports of extramarital flings. He married Previn in 1997, and they have remained together since, adopting two daughters of their own. Allen continued making movies, including ‘Midnight in Paris’ and ‘Blue Jasmine’, throughout the ongoing public debate over his personal life.

13. Mick Jagger

Mick Jagger fronted the Rolling Stones through decades of rock tours and sold-out stadiums. He married model Bianca Jagger in 1971, but their union lasted only until 1978 amid his affairs with women like singer Marsha Hunt and model Jerry Hall. Jagger fathered a daughter with Hunt during that marriage, which added to the strain on his relationship with Bianca.

After divorcing Bianca, Jagger dated Hall for over two decades, during which he had multiple high-profile romances, including one with Brazilian model Luciana Gimenez that resulted in another child in 1999. The Stones kept touring, releasing albums like ‘Bridges to Babylon’ while Jagger balanced fatherhood to eight kids from different mothers. He and Hall parted ways in 1999 after she filed for divorce over his infidelity.

12. Ashton Kutcher

Ashton Kutcher rose to fame on ‘That ’70s Show’ and later invested in tech startups as a venture capitalist. He married actress Demi Moore in 2005 after dating for two years, but their relationship hit rough patches due to his reported affairs with women outside the marriage. One notable incident involved model Sara Leal in 2011, right before their sixth anniversary, which Moore cited in her memoir as part of a broader pattern.

Kutcher and Moore divorced in 2013, and he soon started dating Mila Kunis, his co-star from ‘That ’70s Show’. They married in 2015 and have two children together. Kutcher produced shows like ‘Punk’d’ and advocated for child sex trafficking awareness through his organization Thorn during this time.

11. Alex Rodriguez

Alex Rodriguez dominated baseball with stints on the Yankees and Rangers, hitting 696 home runs over his career. He dated singer Jennifer Lopez twice, first briefly in 2008 and then seriously from 2017, but rumors swirled about his texting with Southern Charm star Madison LeCroy while with Lopez. That led to their 2021 breakup, and earlier relationships like with Cameron Diaz in 2010 ended partly over similar infidelity claims.

Rodriguez also faced accusations during his time with Torrie Wilson from 2009 to 2015, including flings with other women. He transitioned to broadcasting after retiring in 2016 and launched A-Rod Corp to invest in sports teams. Lopez and Rodriguez stayed cordial post-split, collaborating on business ventures.

10. Tiger Woods

Tiger Woods revolutionized golf with 15 major championships and endorsements worth hundreds of millions. In 2009, a car crash outside his home sparked reports of an affair with nightclub promoter Rachel Uchitel, which snowballed into claims from over a dozen women about extramarital encounters during his marriage to Elin Nordegren. Woods held a press conference to apologize, admitting the infidelities stemmed from sex addiction.

Nordegren filed for divorce in 2010, and they share custody of their two children. Woods returned to golf, winning the 2019 Masters after back surgeries, and focused on family life in Florida. His scandal cost him sponsors like AT&T and Gatorade temporarily.

9. John F. Kennedy

John F. Kennedy served as U.S. President from 1961 to 1963, navigating the Cold War and Cuban Missile Crisis. While married to Jacqueline Kennedy, he engaged in numerous alleged affairs, including with socialite Judith Exner, who had ties to the mafia, and White House intern Mimi Alford. Those relationships occurred alongside his political duties, with rumors of up to 30 partners during their marriage.

Kennedy’s brother-in-law Peter Lawford often arranged discreet meetings for these liaisons at the White House or hotels. Jackie stayed with him despite the betrayals, partly for the family’s public image, until his assassination in 1963. Their story inspired books and films exploring the glamour and turmoil of Camelot.

8. Jesse James

Jesse James built a custom motorcycle empire with West Coast Choppers before marrying actress Sandra Bullock in 2005. Shortly after her 2010 Oscar win for ‘The Blind Side’, multiple women came forward with claims of affairs, including tattoo artist Kat Von D’s friend Bombshell McGee, who shared text messages as proof. James entered rehab for sex addiction, but Bullock filed for divorce that same year.

James had three previous marriages, two of which ended amid infidelity accusations from his ex-wives. He later dated Von D briefly and focused on his TV show ‘Jesse James: Outlaw Garage’. Bullock adopted a child during their marriage and kept their Florida home after the split.

7. Bill Clinton

Bill Clinton governed as U.S. President from 1993 to 2001, overseeing economic booms and welfare reform. He admitted to an affair with Gennifer Flowers during his 1992 campaign, which he initially denied, and later faced impeachment over his relationship with intern Monica Lewinsky starting in 1995. Those incidents happened while married to Hillary Clinton, who stood by him through the scandals.

Clinton’s earlier governorship in Arkansas included rumors of other flings, like with Sally Perdue, a former Miss Arkansas. He and Hillary remained married, founding the Clinton Foundation for global health initiatives. The Lewinsky affair resurfaced during Hillary’s 2016 presidential run.

6. Ozzy Osbourne

Ozzy Osbourne fronted Black Sabbath and launched a solo career with hits like ‘Crazy Train’. Married to manager Sharon Osbourne since 1982, he sought treatment for sex addiction in 2016 after affairs with two nannies and a long-term romance with hairstylist Michelle Pugh. Sharon discovered the Pugh affair through emails and briefly moved out, but they reconciled.

Osbourne had a previous marriage to Thelma Riley from 1971 to 1982, marked by his substance abuse and infidelities that led to divorce. The couple shares five children and starred in their reality series ‘The Osbournes’ from 2002 to 2005. Ozzy underwent Parkinson’s treatment while continuing music projects.

5. Kobe Bryant

Kobe Bryant won five NBA championships with the Lakers and became a global basketball icon. In 2003, he faced sexual assault charges from a hotel employee, which were dropped, but he admitted to adultery during the case and faced rumors of over 100 affairs. His wife Vanessa Bryant forgave him, and they renewed vows in 2011 after staying together through the turmoil.

Bryant had dated other women before Vanessa, including Brandy Norwood, with reports of cheating during those relationships. He retired in 2016, launched the Mamba Academy for youth sports, and produced the animated film ‘Dear Basketball’. Tragically, he and daughter Gianna died in a helicopter crash in 2020.

4. Charlie Sheen

Charlie Sheen starred in ‘Two and a Half Men’ and earlier films like ‘Wall Street’. His first marriage to Donna Peele in 1995 ended after 10 months amid reports of his involvement with an escort service. He then cheated on second wife Denise Richards with an assistant in 2006, though he denied it, and faced similar accusations during his 2008 marriage to Brooke Mueller.

Sheen battled substance abuse throughout these relationships, leading to his firing from ‘Two and a Half Men’ in 2011. He has five children from his marriages and dated numerous partners afterward. Sheen appeared in shows like ‘Anger Management’ post-scandal.

3. Brad Pitt

Brad Pitt earned Oscar nods for roles in ‘Once Upon a Time in Hollywood’ and ’12 Years a Slave’. While married to Jennifer Aniston from 2000 to 2005, he filmed ‘Mr. & Mrs. Smith’ with Angelina Jolie, sparking affair rumors that contributed to their divorce. Pitt and Jolie began dating soon after and had six children together before splitting in 2016 amid custody battles.

Before Aniston, Pitt’s engagement to Gwyneth Paltrow ended in 1998 with hints of infidelity on his part. He produced films through Plan B Entertainment, including ‘Moonlight’ and ‘The Big Short’. Pitt focused on winemaking at his French vineyard during personal upheavals.

2. Elizabeth Taylor

Elizabeth Taylor dazzled in classics like ‘Cat on a Hot Tin Roof’ and ‘Who’s Afraid of Virginia Woolf?’. She had eight marriages, including to Conrad Hilton Jr., Michael Wilding, and Mike Todd, during which she pursued affairs that fueled tabloid frenzy. After Todd’s 1958 death, Taylor’s romance with singer Eddie Fisher, who left Debbie Reynolds for her, solidified her reputation for dramatic love stories.

Taylor later married Richard Burton twice after meeting on the set of ‘Cleopatra’, with their open marriage allowing both to have other partners. She advocated for AIDS research through her foundation in the 1980s and 1990s. Taylor passed away in 2011 at age 79.

1. Jude Law

Jude Law gained acclaim for ‘The Talented Mr. Ripley’ and ‘Cold Mountain’. He divorced actress Sadie Frost in 2003 after six years and three children, following years of tabloid reports about his nightlife and flings. Soon after, while dating Sienna Miller during ‘Alfie’, he slept with the nanny caring for his kids, leading her to sell the story to a newspaper in 2005.

Law issued a public apology to Miller during a Donmar Warehouse theater speech, but they broke up shortly thereafter. He dated model Samantha Burke and actress Catherine Harding, fathering more children, and starred in ‘The Grand Budapest Hotel’. Law received a Tony nomination for ‘The Front Page’ in 2016.

Which of these celebrity stories surprised you the most? Share your thoughts in the comments.