Hollywood's Most Notorious Rumored Serial Cheaters

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Few celeb-centric stories manage to rile the masses like those involving relationships and romance, especially when those stories involve extramarital affairs or some other form of infidelity. President Bill Clinton's liaison with Monica Lewinsky during the late 1990s didn't just cause issues for him politically — it was a tabloid scandal on a worldwide scale. Similarly, the drama that emerged between Brad Pitt, Jennifer Aniston, and Angelina Jolie in the 2000s became one of the more infamous love triangles in the Tinseltown annals.

These days, the blowback when a celeb strays from their significant other is swifter and more severe thanks to the 24/7 news cycle and the proliferation of social media. As ever, though, the potential for bad publicity isn't always enough to stop stars with wandering eyes from hooking up behind their partners' backs. Some of those reported adulterers even find themselves labeled repeat offenders when rumors of their misdeeds grow in scope.

From Hollywood's biggest names to golf's most decorated champion, the celebs on this list are alleged (and, in some cases, confirmed) to have cheated on their partners more than once, and/or with multiple different people.

From humble beginnings as an oft-overlooked member of "Saturday Night Live's" B-team to selling out arenas and being involved in what may just be the most infamous moment in Oscars history, Chris Rock's show business journey has been something to behold. Now, four-plus decades after he took his first steps into the world of standup comedy, the Brooklyn native has entrenched himself as a comedy legend akin to performers like Richard Pryor, George Carlin, and Lenny Bruce.

However, Rock has faced turmoil behind the scenes, and, specifically, in his relationships, due to his own confirmed and rumored infidelity. The "Grown Ups" star was married to Malaak Compton, with whom he shares two children, for 20 years (from 1996 to 2016), but sought the company of other women throughout their partnership. He spoke out about his activities on his 2018 Netflix comedy special "Tambourine," saying (via E! News), "It's my fault, because I'm a f***ing a**hole. I didn't listen. I wasn't kind. I had an attitude, I thought, 'I pay for everything, [so] I can do what I want.' That s*** don't f***ing work! I just thought I was the s***."

Rock admitted to sleeping with multiple women while he was married to Compton. His history of cheating scandals includes a long-rumored romance with actress Kerry Washington. Neither Rock nor the "Django Unchained" star has publicly confirmed their involvement with one another.

Few actors have ever reached the iconic status of Elizabeth Taylor; a prime candidate for Hollywood's Mount Rushmore thanks to legendary performances in 1944's "National Velvet," 1959's "Suddenly, Last Summer," 1963's "Cleopatra," which was the most expensive film ever made at the time, and a multitude of others. Meanwhile, the two-time Oscar winner's personal life was every bit as eventful, if not more so.

Taylor was married a whopping eight times to seven different men from 1950 (when she was just 18 years old) to 1996. Her husbands included legendary performers like singer-actor Eddie Fisher and two-time spouse and frequent co-star Richard Burton, a veritable tycoon in Conrad "Nicky" Hilton, Jr., and politician and U.S. Naval secretary John Warner, among others. However, Taylor's rumored relationships further delve into extramarital territory.

As reported by the Huffington Post in 2012, biographers Danforth Prince and Darwin Potter alleged in their book "Elizabeth Taylor: There is Nothing Like a Dame" that Taylor had an affair with fellow actor and future president Ronald Reagan. The authors further claimed that Taylor once had a threesome with President John F. Kennedy and actor Robert Stack when both were married. Other alleged lovers include Tony Curtis, Errol Flynn, Peter Lawford, and Paul Newman.

Maybe the most infamous serial cheater in modern entertainment history, golf legend Tiger Woods had been noted primarily for his otherworldly domination of the links and his seemingly squeaky-clean image throughout his career until everything came crashing down in November 2009. That month, the National Enquirer published a story claiming that Woods, who was married to model Elin Nordegren at the time, had an extramarital relationship with Rachel Uchitel (who was then a New York City nightclub manager). Shortly thereafter, Woods crashed his Cadillac Escalade near his home in Florida, leading to speculation about his alleged affair and the events leading to the accident.

"I have not been true to my values and the behavior my family deserves," Woods said in the days after the accident (via Reuters). "I have let my family down and I regret those transgressions with all of my heart." That list of transgressions grew almost by the day as the details to come out about Woods' cheating scandal went beyond sensational territory and into the realm of the unbelievable. As reported by the National Enquirer (via the New York Post), Woods allegedly confessed to having affairs with some 120 women, including the young daughter of one of his and Nordegren's neighbors. The couple divorced in 2010.

Woods' reputation has never fully recovered in the years since, and despite some big moments, such as winning the Masters in 2019, his career has similarly failed to reach its pre-scandal heights. 

In that period of time between Hugh Grant's headline-making sexual excursion while partnered with Elizabeth Hurley in the mid-1990s and the revelation of Tiger Woods' mass infidelity in 2009, Jude Law's split with Sienna Miller may have been the most infamous cheating scandal to emerge. In July 2005, Law issued a public apology when it was revealed that he was involved in an affair with his children's nanny.

The mass reporting of the incident was particularly rough for the stars to navigate, with Miller calling it "one of the most challenging moments I hope I'll ever have to experience" during a 2020 interview with the Daily Beast (via Grazia magazine). "With that level of public heartbreak, to have to get out of a bed let alone stand in front of 800 people every night, it's just the last thing you want to do," she told the outlet. However, Law's fling with the nanny wasn't the first time infidelity was part of his story.

Prior to his divorce from Sadie Frost in 2003, there were rumblings of an on-set affair between Law and his "Cold Mountain" co-star Nicole Kidman. Among the tabloid claims making rounds at the time was that Kidman led Law to cheat, as noted by The Guardian. Kidman sued the Daily Mail over its affair story, winning damages for libel as a result. However, speculation about Law's activity outside of his relationships continues even now.

His name may not hold the same cachet now, but for people of the early-to-mid 2000s, Jesse James was reality television's wrench-wielding, tattoo-covered king of cool. His show "Monster Garage," which saw mechanics modify vehicles into unique and monstrous creations, aired for five seasons (from 2002 to 2006) on the Discovery Channel and was one of cable TV's early reality hits. He also famously founded West Coast Choppers.

James' life outside of the garage was an entirely different kind of high-octane. The Long Beach native famously married Hollywood star Sandra Bullock in 2005, a partnership that would last nearly five years until they were divorced in June 2010. Their marriage didn't end with a whimper, either. Earlier that year, the couple had been working to adopt a child together when they suddenly found themselves embroiled in a cheating scandal that became international news. Michelle McGee, then a San Diego-based tattoo artist, came forward with claims of a long-term affair with James, selling her story to a tabloid.

In the days following the initial revelation, multiple other women came forward with claims of their own. James later apologized to Bullock and said his extramarital activity was motivated by past trauma. "I think I do things to sabotage my life, including having extramarital affairs, texting, overworking myself, injuring myself, doing stunts and stupid things," he said (via NBC Philadelphia). "I think I do a lot of things in my life that I shouldn't be doing that aren't conducive to being a perfect husband."

As an actor and television personality, Dean McDermott is well-known to Canadian audiences. The Toronto native served as the host of "Chopped Canada" for two of the series' four seasons during the mid-2010s. And, before that, he played the recurring role of Constable Renfield Turnbull on the CTV/CBS series "Due South." At this point, though, he may be best known to entertainment fans as the former husband of "Beverly Hills, 90210" star Tori Spelling.

The relationship between McDermott and Spelling was notably born from infidelity. The two stars originally met in mid-2005 on the set of the Lifetime movie "Mind Over Matter," when they were both married to other people and subsequently spent the night together in a hotel room. "It was love at first sight. I fell so hard ... Then I noticed he had a wedding ring," Spelling wrote in her 2009 memoir "sTORI Telling" (via Fox News), adding, "Oh, yeah — I had a husband too." 

Fast-forward to 2013, and a woman nearly 20 years his junior named Emily Goodhand told Us Weekly that she had engaged in an affair with McDermott, who later apologized and entered rehab. "I am truly sorry for the mistakes I have made and for the pain I've caused my family," he said in a statement to People (via The Christian Post). The couple ultimately separated in 2023 after 18 years together, later divorcing.

For more than three decades, David Letterman carved out a legacy for himself as a comedic icon on the late-night television scene. Beginning with his run on NBC's "Late Night" from 1982 to 1993, Letterman reinvigorated a format that had largely existed in Johnny Carson's shadow. He continued to serve as one of late night's pillars after launching the "Late Show" on CBS, a post he held from 1993 to 2015.

And while Letterman's flair for the wild and absurd made him a hit during his NBC days, it paled in comparison to what was going on behind the scenes later in his career. In 2009, Letterman revealed to his audience that he had testified before a grand jury following an extortion attempt. As reported by ABC News, the late-night host received a package containing a threat to reveal his serial infidelity with female staffers unless he paid a large sum of money (later revealed to be $2 million). Letterman, who had dated his wife, Regina Lasko, for years before their 2009 marriage, ultimately copped to the infidelity himself.

"I have had sex with women who work on this show. And, would it be embarrassing if it were made public? Perhaps it would," Letterman said (via Andrew Cantu on YouTube). "Especially for the women." CBS News producer Joe Halderman was later found guilty of attempted extortion and sentenced to six months' imprisonment. Despite his affairs and the publicity firestorm Halderman's extortion attempt sparked, Lasko has remained married to Letterman.

For book and movie fans of a certain age, the supernatural love story between Edward Cullen and Bella Swan in Stephanie Meyer's "Twilight" series is the gold standard for romance in fiction. And the mystique surrounding their relationship was bolstered by a burgeoning romance between the actors who brought the characters to life on the big screen: Robert Pattinson and Kristen Stewart. Alas, Pattinson and Stewart's relationship didn't have the same happy ending as Edward and Bella's; instead, it was the first act in a real-life story that saw Stewart branded a cheater.

As relayed by People, Stewart issued an apology to Pattinson in 2012 when it was revealed she had an affair with Rupert Sanders, who directed her in the film "Snow White and the Huntsman." "This momentary indiscretion has jeopardized the most important thing in my life, the person I love and respect the most, Rob. I love him, I love him, I'm so sorry," Stewart said in a statement (via People). However, this wouldn't be the last time the "Love Lies Bleeding" star would find herself at the center of a cheating scandal.

Per a 2017 Radar Online report, Stewart was snapped spending the night at the Los Angeles home of her former partner, Alicia Cargile, while she was still in a relationship with model Stella Maxwell. "Alicia is the first woman that Kristen has ever loved and she will always love her," a friend reportedly told the outlet. Stewart is now married to screenwriter Dylan Meyer.

For 13 seasons from 2011 to 2025, Tristan Thompson lived the NBA dream, winning a championship beside LeBron James as a member of the 2016 Cleveland Cavaliers and starting in 478 of his 819 career games in the Association. For all he did on the hardwood, though, the University of Texas alum was arguably more prolific in his off-the-court activities, where his serial cheating was fodder for a tabloid firestorm.

Thompson became a crossover celebrity in 2016 when he was linked to reality star, socialite, and model Khloé Kardashian. And while the two were never wed, their on-again, off-again relationship lasted for five years, during which they welcomed two children together. Their partnership was dealt a crippling blow, though, in February 2019 when Thompson was unfaithful with Jordyn Woods, then the best friend of Kardashian's youngest half-sister, Kylie Jenner.

Thompson and Kardashian attempted to keep their relationship afloat over the next handful of years, but its death knell ultimately came in 2021 when it was revealed that the NBA star was expecting a child with another woman. "The second time, you know, my surrogate was still pregnant with (their son) Tatum, and the people didn't know yet that I was having Tatum," Kardashian recalled while guesting on Jay Shetty's "On Purpose" podcast (via People) in 2025. "But I felt such shame that it was happening again, because I knew I knew better."

Self-professed Lord and reality star Scott Disick is another person whose star cred was sent into a higher orbit thanks to his relationship with a Kardashian. From 2006 to 2015, he was in a relationship with Kourtney Kardashian, with whom he shares three children. However, their long-term partnership was turbulent at times, in part due to Disick's alleged infidelity. As noted by Complex, Kardashian found romantic messages between Disick and another woman during the filming of "Keeping Up with the Kardashians'" second season in 2007.

Then, in 2015, Disick was snapped getting cozy with his alleged ex-girlfriend, stylist Chloe Bartoli, in France. Although he continues to be part of "The Kardashians" universe, Disick and Kourtney ultimately ended their romantic relationship later that year. Nevertheless, additional accusations of cheating have become part of Disick's extensive dating history. 

In the years after his split from Kardashian, he eventually got into a relationship with the much younger Sofia Richie, but the pairing didn't last. "He cheated on her, and she confronted him," a source with knowledge of the relationship reportedly told People in 2018, adding, "Lionel [Richie] knows Scott's playboy ways, and he doesn't want to see his daughter get hurt."

In the final years of his Hall of Fame-worthy baseball career, during which he belted 696 home runs and won three MVP trophies, Alex Rodriguez was branded a cheater due to his use of performance-enhancing drugs. Rodriguez first admitted to using steroids in 2009, before admitting to further usage during Major League Baseball's Biogenesis scandal in 2013-14 (which resulted in a one-year suspension from the league).

Rodriguez similarly faced high-profile cheating allegations in his personal life. As chronicled by People, Rodriguez's former wife, Cynthia Scurtis, reportedly found him in bed with another woman in 2007. The following year, the legendary shortstop/third baseman was romantically linked to pop icon Madonna, despite still being married. However, both parties denied that an affair had taken place. Rodriguez was also snapped partying with other women during the marriage. The couple divorced in 2008 after five years together.

More recently, it was rumored that Rodriguez was unfaithful to his former fiancée and pop star Jennifer Lopez during their long-term partnership. When asked about those rumors during a 2025 appearance on "Watch What Happens Live," Lopez responded, "I really have nothing to say about my personal life anymore. I feel like it's ... I'm done with that." Four years earlier, Rodriguez was rumored to have slid into the DMs of "Southern Charm" star Madison LeCroy. In any case, A-Rod and J-Lo officially split in 2021.