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10 Celebrity Boyfriends Who Cheated On Their Significant Others

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10 Celebrity Boyfriends Who Cheated On Their Significant Others

Everyone can agree that cheating is the worst thing you can do as a partner. It can be the ultimate relationship betrayal and breaks the trust, which means you may never be able to go back to the way things were.

And even if the one who is cheated on decides to take the offender back, there will always be that thread of mistrust and suspicion running somewhere in the back of their minds. The damage has already been done, so to speak. 

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Unfortunately, cheating has become a very common thing in relationships with both genders being guilty of commiting the heinous offense on their partners, and it is often the downfall of many a couple.

Even in the celebrity world, infidelity has become a frequent toppling of quite a few of our favorite famous couples. Yes, not even glamorous celebs can escape this relaionship problem!

A while ago, Cameron Diaz herself even made a media splash after claiming that everyone will get cheated on at some point. She was quoted as saying, "Everybody has been cheated on, everyone will be cheated on. I can't fix that, I don't know how, I don't have any judgement on anybody, I don't know how to fix the problem." 

Yikes! While that may seem like a bit of a dark, pessimistic look at love and relationships, we can also sort of almost see where she's coming from.

Infidelity is one of the most common reasons why couples tend to split up, and we're sure that, as a celeb, especially, Diaz has probably seen her own fair share of cheaters throughout her career. 

Diaz then tried to somewhat soften the blow of her statement by adding, "We are human beings, we are complicated. You cannot go through life without tallying up a few scars; you cannot go through life unscathed."

And while we hope that those scars won't include a relationship where cheating is involved, it's still hard to ignore just how frequently infidelity has ruined a couple's chance at having a happily ever after. 

However, while we do think that Diaz's words tend to teeter on the extreme side, there are certain cheaters who have proved that she may not be entirely incorrect in her assumption.

Even these beautiful famous ladies felt their relationships crumble at the hands of their cheating boyfriends.

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While you'll probably wonder how anyone could even begin to think about cheating on someone like Rihanna or Jessica Biel (seriously, guys?), this has sadly happened to even some of the world's most gorgeous, high-profile women.

What were these guys thinking?

This is a question that we'll probably never be able to figure out. It's just one of those mysterious things in life. You may be familiar with some of these celebrity cheaters, but, then again, you may not have even known that they committed the ultimate betrayal.

So, are you surprised by any of these 10 celebrity men who cheated on their girlfriends? Let's take a look at this list of notorious Hollywood cheaters and find out.

Jude Law

Photo: Steve Finn/Getty Images
10 Celebrity Boyfriends Who Cheated

Law was engaged to Sienna Miller when he famously cheated with his children's nanny, Daisy Wright. After the tabloids exploded with news of his infidelity, the actor made a public apology to his fiancee.

The two never wed, but Miller eventually said they had moved on from the incident, saying, "We don't see each other that much. I care about him enormously."

Justin Theroux

Photo: Brad Barket/Getty Images
10 Celebrity Boyfriends Who Cheated

Before Jennifer Aniston came along, Justin Theroux was living with his girlfriend of many years, Heidi Bivens. When Aniston and Theroux met on the set of Wanderlust in 2010, he was still living with Bivens.

But rumors soon swirled that he was cheating on her, although Biven's mom had denied his involvement with Aniston.

When J + J finally came out as a power couple, Bivens had just moved out of the NYC apartment she shared with Theroux. Lines are blurry, but it looks like Jen took a play from the Angie handbook.

David Letterman

Photo: Kris Connor/Getty Images  
10 Celebrity Boyfriends Who Cheated

The Late Show got way more exciting when Letterman went on-air to apologize for sleeping with multiple women on his staff, and cheating on longtime love, Regina Lasko, the mother of his young son.

Although the two weren't married at the time of his affair with assistant Stephanie Birkitt, they wed six months prior to the scandal breaking, and Letterman was still deeply remorseful to lasko for his actions. The truth came out after former CBS employee Joe Halderman attempted to blackmail and extort $2 million from Letterman to keep quiet about his affairs.

Halderman pleaded guilty for attempted grand larceny and spent several months in prison. Letterman and Lasko stayed together, and he says he's still working on the marriage. 

Rob Kardashian

Photo: Michael Buckner/Getty Images
10 Celebrity Boyfriends Who Cheated

Back in 2009, reality star Rob Kardashian and Adrienne Bailon ended their relationship after two years. It wasn't until he came clean on Keeping Up With the Kardashians that his infidelity was confirmed.

Bailon revealed on her talk show The Real that she wrote a fake letter from a fake boyfriend to get Kardashian to leave her alone.

"What all ya'll thought was that it was written by my boyfriend. It was not written by a boyfriend. That was written by me and my girl sitting on the sofa one day deciding to ourselves, 'Well, how can we make him stop calling me?'" she revealed.

Keith Urban

Photo: Michael Loccisano/Getty Images
10 Celebrity Boyfriends Who Cheated

Twenty-three-year-old model Amanda Wyatt claimed she had an affair with Keith Urban throughout the beginning of his relationship with current wife, Nicole Kidman.

She revealed, "He used to call me and tell me how much he missed me making him laugh. Whenever he came home to Nashville, we'd get together. I never pressured him to commit."

Even after the allegations, Kidman stayed by her boyfriend's side, and the couple has since wed and welcomed two daughters.

Chris Brown

Photo: Getty
10 Celebrity Boyfriends Who Cheated

Chris Brown admitted to his infidelity in an interview with Power 105.1. He confessed, "I already had two girls at one point. It was honest. I'm at that point [of being faithful]."

In the same interview, he said that he would not be okay if Rihanna had another partner, unless it was a girl. What a classy couple. 

Hugh Grant

Photo: Getty
10 Celebrity Boyfriends Who Cheated

One of the most infamous cheating scandals that happened was when Hugh Grant pleaded no contest to misdemeanour lewd conduct after being caught with his pants down — literally — with Hollywood sex worker, Divine Brown.

Although girlfriend Elizabeth Hurley stayed by his side, the couple eventually split in 2000. Eventually, Grant owned up to his one-night stand and said, "I just said, ‘I did it.'"

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Justin Timberlake

Photo: Getty
10 Celebrity Boyfriends Who Cheated

Although the famous couple were on-again/off-again at the time, heavy rumors suggested that while still dating, Timberlake had an affair with Olivia Munn after meeting at a MySpace event. Supposedly, he sent her messages claiming that he and Biel were over.

To this day, JT denies the claim and Munn has made no statement about the incident. Timberlake and Biel married two years after the scandal. 

Liam Hemsworth

Photo: Getty
10 Celebrity Boyfriends Who Cheated

Did Liam Hemsworth stray with January Jones? Tabloids went crazy after rumors started flying about Liam and January spending the night together after the 2013 Oscars.

Although it was never confirmed, Jones didn't exactly ever deny it, either.

Billy Bob Thornton

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10 Celebrity Boyfriends Who Cheated

Angelina Jolie must have a thing for men with girlfriends.

In 1999, Billy Bob Thornton was living with girlfriend Laura Dern when he starred in the movie Pushing Tin with Angelina. Dern was away on a shoot at the time Thorton and Jolie got together, and she later told the press, "I left our home to go and make a movie and while I was away my boyfriend got married, and I never heard from him again."


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Lindsey Kupfer is a Celebrity Reporter for the New York Post's PageSix.com and freelance writes in her free time. She has previously written for Seventeen, Tiger Beat and The Frisky. 

Editor's Note: This article was originally posted in April 2014 and was updated with the latest information.