Busted! 25 Celebrities Who Were Caught Cheating With Their Pants Down

Jay Dawson November 25th 2016 Entertainment
It’s hard to say what inspires people to go out and hurt the ones they love – or claim to love. It’s even harder to fathom the idea of keeping up a secret affair, month after month, when you could just break up with your original partner. But whether it was a chance meeting or deliberate act, these stars just couldn’t seem to resist the illicit chemistry. That is, of course, until they were caught. Most of them were ashamed. A few of them got away with it. And some, it seems, couldn’t even care less.

1. Billy Bob Thornton

There are a few ways to find out that your partner is cheating on you. You could surprise them in bed together, hire a private detective, even discover a well-worn love letter (or just a dirty text). Or you could be Laura Dern, who found out Billy Bob Thornton was cheating on her when she arrived home one day. The house was empty, and in her absence he had gotten married to Angelina Jolie. Ouch.

2. Kristen Stewart

Maybe having a stormy relationship on-screen doesn’t set the best example for your off-screen relationships. Kristen Stewart and Robert Pattinson were a tabloid highlight for years as they negotiated their rocky romance, but it all finally came apart when she was caught cheating with director Rupert Sanders. Who’s married. We don’t know if that makes it better or worse.

3. Kris Jenner

You could fill an internet with Kardashian-related scandals, but we’ll choose this one because it’s frankly bizarre. The affair itself is fairly run-of-the-mill: Kris Jenner has a steamy affair behind the back of husband Robert Kardashian, yadda yadda yadda. The weird part is that she took her daughter, Khloe, on some of these secret rendezvouses, forbidding her to tell the truth about it to Robert. Truly strange, and a little bit sick.

4. Arnold Schwarzenegger

Five years ago, the world (well, some of us) recoiled in horror when it was found out that Arnie had been sleeping with his housekeeper for over a decade. Not only that, he had a teenage son with her who had been kept a secret all this time. It’s hard to believe that his wife, Maria Shriver, never knew. It’s even harder to believe that Arnie could act so well.

5. Britney Spears

According to Spears’s ex-boyfriend Jason Alexander, Britney cheated on Justin Timberlake a whole bunch of times, way back in the early 2000s. It’s a juicy story, but it tastes a little like sour grapes to us. It doesn’t quite ring true. Who would cheat on Justin Timberlake, anyway?

6. Hugh Grant

In one of the more baffling cases of celebrity cheating, Hugh Grant was caught paying for sex when he had the very free and very beautiful Liz Hurley waiting for him at home. We understand that after eight years the bedroom excitement could have fizzled. But it was probably better to work it out than to get caught red-faced and red-handed.

7. Jennifer Lopez

There weren’t many good things that came from the set of Gigli. The film was a box-office and critical flop, and most people quickly decided to forget it ever happened. J-Lo won’t forget it, though: her marriage to Chris Judd came to a screeching halt when she was caught having an affair with co-star Ben Affleck.

8. Bill Clinton

Has this one been done to death yet? Are we flogging a dead horse? Is there anyone on the planet who doesn’t know the events surrounding Bill Clinton’s affair? The answers, of course, are yes, yes, and no. And while we’re at it, spare a though for Monica Lewinsky, who went through hell and came out fighting.

9. Heidi Klum

Many of us thought that the Klum-Seal marriage was forever. They were our rock, a match made in heaven, a perfect voice with a perfect figure, and they renewed their vows every year. When we all found out that Klum had cheated on him with her bodyguard, and that their fairytale marriage was over, our world came crashing down.

10. Ashton Kutcher

Amid the gossip and bitchiness, we secretly hoped that Ashton Kutcher and Demi Moore would keep their marriage together. It would be proof that love could bloom in the face of the naysayers. Sadly, Ashton went and wrecked it all on the virtually unknown Sara Leal. What a waste.

11. Brad Pitt

While he wasn’t exactly “caught”, the circumstances of his separation with Jen-Ton are highly suspicious. What we do know is that they were divorced the same year that he both starred with and started dating Angelina Jolie. Which didn’t last, either. Although clearly not much ever does in Tinseltown.

12. Tiger Woods

Nobody could blame Elin Nordegren (in fact, everyone silently cheered) when she brandished a golf club, chased Tiger Woods out of his house, then smashed up his car. We’d feel like doing the same thing if we found out that after five years of marriage, our partner had slept with almost anyone who asked. The craziest thing about it is that his reputation never suffered.

13. Diddy

While he’s still got his baying legion of fans, serial cheater Diddy has lost the faith of many of his girlfriends and lovers. He slept around while with Kim Porter, and even squeezed in a relationship during one of their mini-breaks. Around that time, he started seeing J-Lo, who also realized he was cheating on her. Cheating on someone you’re cheating with, who’s just a side dish for someone else you’re cheating with and oh god, it’s worse than Inception.

14. Woody Allen

The details of Woody Allen’s affair might be less seedy than they seem, but they still somehow leave a bad taste. He was caught cheating on his long-time partner Mia Farrow with Mia’s adopted daughter Soon-Yi Previn. Although Woody and Mia were never married, and Soon-Yi was from a previous relationship of Mia’s (and never adopted by Woody), and Woody and Soon-Yi now live happily ever after, we’re still a bit weirded out.

15. Jude Law

We don’t know what’s so alluring about household staff, but Jude Law hasn’t been able to help himself dipping into the workforce, either. The British actor was caught red-handed by Sienna Miller, his fiancé at the time, getting some physical attention from his children’s nanny. Unsurprisingly, they split up soon after. Far more surprising was that four years later, Siena gave him a second chance.

16. Sienna Miller

Here’s a story that will warm the cockles of your heart. Fresh and smarting from Jude Law’s infidelity, Sienna decided to have a spin of the wheel herself. Her revenge was far sweeter, though, as she hooked up with Daniel Craig, better known as 007. It’s clearly the better deal - we haven’t seen pictures of the nanny, but we doubt she’s got a six-pack like Craig’s.

17. David Letterman

Letterman’s late night show was always filled with bizarre episodes, feuds, and interviews gone wrong. But the biggest plot twist of all came when a fellow CBS employee accused Letterman of having affairs with several staffers, and attempted to blackmail him for $2 million. Letterman was forced to admit the affairs on-air, but somehow he came out on top – the man was arrested, his wife forgave him, and the audience cheered him on the whole way.

18. Kobe Bryant

When Kobe Bryant was arrested and subsequently revealed to be cheating on his wife, he pulled the classic celeb “dazzle and awe” maneuver and hushed his wife’s doubts with a $4m piece of jewelry. He didn’t bother trying to perform the “penitent man”, though, and was caught cheating on her again a couple of years later. Finally, his wife Vanessa got smart and did the old “vanishing spouse”.

19. Ethan Hawke

Yet another celeb who’s followed the siren call of the hired help, Ethan Hawke thoroughly wrecked his marriage to Uma Thurman by having a tryst or three with the nanny. At least he followed through with the fling – five years after the divorce, Ethan ended up getting married to the nanny.

20. Anne Heche

Heche is a chameleon of the acting world, hopping from role to role in both film and television. It seems like she’s hopping from bed to bed, too, with a couple of high-profile cheating scandals. First, she cheated on her partner of three years, Ellen DeGeneres, with cameraman Coleman Laffoon. After she and Laffoon got married, she did it again six years later with actor James Tupper.

21. Larry King

83-year-old media star Larry King has had his fair share of ladies, having been married an incredible eight times. But it seems he just can’t get enough. Scandal arose a few years ago when it was found that he was cheating on his current wife, Shawn Southwick, who’s 26 years younger. Guess who it was with? Her little sister.

22. Luke Worrall

If someone cheats on you, it’s hard to be the sensible, rational adult. And we’re not blaming Kelly Osbourne for her two-timing boyfriend, British DJ Luke Worrall, ending up in bed with a transgender woman. We know he wronged you. But ending the relationship publicly and messily on Facebook? That’s just childish.

23. Two of Halle Berry’s partners

Poor Halle. Even being cheated on once would be enough to undermine your confidence, but the talented actress has had it done to her twice. The first was while she was dating MLB player David Justice, and the second when she was with R&B singer Eric Benét. It’s amazing she can keep on loving.

24. Jack Nicholson

Brilliant, but also old and a little bit strange, we’re not entirely sure who Jack Nicholson could cheat with. He must have had something going for him, though, because he chose to sleep around on the luminous Anjelica Huston, which was understandably the end of their relationship. There was no way he could deny the evidence – his fling, Rebecca Broussard, was now visibly pregnant with his child.

25. Frank Sinatra

Cheating seems to be an eternal human impulse – just ask Frank Sinatra (if you could). Caught up in the Rat Pack and restless energy of showbiz, he was discovered to be carrying on an illicit affair with Hollywood doyenne Ava Gardner. Even without Twitter and Facebook, the result scandalized the nation. And earned him a divorce.

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