Top 10 Celebrities Who Cheated on Multiple Partners

After his divorce from Sadie Frost in late-2003, this English actor wasted no time starting another relationship. Law began a courtship with co-star Sienna Miller on the set of “Alfie,” a movie where he plays a womanizing limo driver who begins a relationship with Miller’s character. Spoiler alert: in an unfortunate instance of foreshadowing, Law’s character distances himself from Miller’s and beds another woman. A couple of years and an engagement later, Law seemed to reprise his role as Alfie, ultimately distancing himself from Miller and sleeping with his children’s nanny. Law apologized for the affair, but never managed to permanently fix the damage with Miller, and today he’s got five children by three women – none of whom is his girlfriend.

One of the biggest stars from the Golden Age of Hollywood, this beautiful brunette was famous for her eight marriages and wild relationships. After her third husband died tragically in a plane crash, she found solace in the arms (and bed) of her friend Eddie Fisher, who was married to her friend Debbie Reynolds at the time. After eventually marrying Fisher, Taylor had a well-publicized affair with actor Richard Burton while filming “Cleopatra.” She then ended up divorcing Fisher and marrying Burton just 9 days later. The fun didn’t stop there, though, as Liz and Dick’s ‘marriage of the century’ was mired by countless allegations of affairs on both sides, and even reports of an open marriage.

While this one still hasn’t been proven, we at least know that something was going on between Brad Pitt and Angelina Jolie on the set of “Mr. & Mrs. Smith” back in 2005. After 5 years of marriage to Pitt, Jennifer Aniston filed for divorce, and a mere month later, Pitt and Jolie were spotted together overseas. Dubbed ‘Brangelina’ by the media, they announced the arrival of their first child together soon after. Pitt still denies having an affair with Jolie, but admits he did fall in love with her while they filmed together. Fast-forward 11 years, and it’s Brangelina that’s divorcing, while Jennifer Aniston is happily re-married.

From shooting a fiancée in the arm, to dating numerous porn actresses, Charlie Sheen’s relationships have been tumultuous to say the least. He and his first wife divorced after his name popped up on the client list of a well-known escort agency. Although he’s vehemently denied it, rumor has it Sheen cheated on his second wife, Denise Richards, with his assistant – but it was his drug and alcohol problems that caused them to split. His third wife, Brooke Mueller, didn’t escape Sheen’s extra-marital escapades either, as he was alleged to have had an affair with lingerie model and part-time escort, Angelina Tracy. After that divorce, he did himself a favor and stayed unmarried. That was probably a #winning decision.

To cheat is one thing, but for your wife to find out about it as you’re arrested for rape is another. In 2003, it was alleged that Kobe Bryant sexually assaulted a 19-year-old employee at the Colorado hotel he was staying at. During proceedings, the NBA all-star also came clean about another affair he was having at the time. Tip of the iceberg? Well, rumors have circulated that he’s had affairs with over 100 women. Luckily for him, his sexual assault case was dropped because the accuser wouldn’t testify, but Kobe did admit his infidelity. Even luckier though was that, through it all, his wife, Vanessa, stayed by his side, hopefully because he decided to keep his scoring strictly on the court.

Despite Ozzy’s high-profile alcohol and drug addictions, the Godfather of Heavy Metal has had a fairly stable relationship with wife Sharon since 1982. Well, at least that’s what we thought. It turns out he’s been undergoing therapy for yet another addiction: sex. Sharon seemingly forgave him for his numerous slip-ups, which included sleeping with at least two of the family’s nannies, but it wasn’t as easy to forget his full-fledged affair with hairstylist Michelle Pugh. Even Kelly Osbourne laid down some wrath by apparently tweeting Pugh’s personal phone number, accompanied by some harsh words. The Osbournes swear the Pugh affair was just an addiction-fueled mistake, but Pugh says it was long-term, and the best love of her life.

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#4: Bill Clinton

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No, not even presidents are exempt from this list, and this one in particular has definitely felt the heat. There have been allegations against President Clinton of affairs, rape, and sexual harassment from many women over the years, but Clinton has admitted to consensual extramarital activity with Gennifer Flowers and more famously Monica Lewinsky. Clinton initially denied being with Lewinsky, which led to perjury charges and impeachment. But Slick Willy slipped out of the ordeal pretty much unscathed, as he kept the presidency and his wife, Hillary Clinton. In 2016, presidential candidate Donald Trump brought up the scandal again, to try to discredit HRC as she ran for president. Interestingly enough, it probably ended up hurting her more than Bill, politically.

He married Sandra Bullock in 2005, but it wasn’t until 2010 that many women came out claiming to have had affairs with James. The most prominent was perhaps tattoo artist and model Bombshell McGee, who released text messages confirming the affair. The news came out just days after Bullock was on a high from winning the Oscar for Best Actress for “The Blind Side.” James then confessed his transgressions to his wife and checked into rehab to try to keep his marriage afloat, but America’s Sweetheart wasn’t having it, and filed for divorce, keeping sole custody of the boy they had adopted together.

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#2: John F. Kennedy

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When you hear stories about the White House in the early ‘60s, it sounds more like a party house than the nation’s executive office at the height of the Cold War. President John F. Kennedy was – by all accounts – happily married to Jackie, but the number of allegations of extramarital affairs leveled against him surpassed even Bill Clinton’s. From reportedly bedding possible Communist spies, to theoretical threesomes with staffers nicknamed Fiddle and Faddle, the unconfirmed rumors were all fascinating; but JFK’s most high profile supposed affair was – of course – with Marilyn Monroe. According to some sources, Jackie wanted a divorce, but was offered money to stay and protect the president’s image.

Before we unveil our top pick, here are a few honorable mentions:
- Mick Jagger
- Lamar Odom
- Ashton Kutcher

Just two days after the National Enquirer published a story about an affair between Tiger Woods and nightclub manager Rachel Uchitel, the golfing legend crashed his Cadillac Escalade into a fire hydrant and tree near his home in the wee hours of the night. Police suspect the story caused a fight with wife Elin Nordegren, which led to the accident. Shortly after, a voicemail message was released and the Tiger was caught. Over a dozen other women then came out, claiming they’d had affairs with Woods. He admitted his infidelity, but Nordegren divorced him soon after. And, as it turns out, it wasn’t just the relationship that suffered as a result of his philandering: shareholders in Woods’ sponsor companies lost an estimated $5-$12 billion.

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