• Wed, Sep 3 - 5:30 pm ET

9 Weirdly-Successful Celebrity Relationships That Started With Cheating

Adam Scott I don't get it at all GIF Parks and Recreation

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Being a celebrity is already like living under the weirdest kind of microscope, so it always amazes me when two famous people are able to make a relationship last. But as if that wasn’t already mind-boggling enough, there are actually couples out there that began their relationships with infidelity AND SOMEHOW STILL MADE IT WORK. How is that even possible?

I just feel like if you and your partner are starting things out with cheating right off the bat, you’re pretty much doomed to failure, right? That’s what all the rom-coms taught me growing up! But this is apparently one of those situations where art doesn’t necessarily imitate life, because these celebrity couples who started their relationships out with cheating and were weirdly-successful regardless. Doesn’t mean they’ll make it long term or even that they’re still together now, just that they blew our mind by lasting more that forty-five seconds.

1. Brad Pitt and Angelina Jolie

angelina jolie and brad pitt maleficent premiere

(Photo: Adriana M. Barraza / WENN.com)

Say hello to your poster children, ladies and gentlemen! As we’ve all heard ad nauseam for the past ten years, Brad was married to Jennifer Aniston when he first met Angelina while costarring with her in Mr. & Mrs. SmithThey both insist that although they fell in love on set, nothing physical happened, but Brad and Jen filed for divorce shortly afterward. Cut to ten years later, Brangelina is recently married with six kids and one of the most rock-solid relationships in Hollywood. Who woulda thunk?

2. LeAnn Rimes and Eddie Cibrian

LeAnn Rimes and Eddie Cibrian on Extra

(Photo: WENN.com)

Honestly can’t believe I’m putting them on a list of successful relationships, but they plaster their lovey-dovey happiness all over social media so often that I was bound to buy into it eventually. When Eddie and LeAnn began their affair in 2009, they were both still married to other spouses — Eddie to Brandi Glanville, from the Real Housewives franchise, and LeAnn to Dean Sheremet. But even though they crash-and-burned two separate marriages to be together, they’re somehow still going strong, having been married to each other since 2011.

3. Tori Spelling and Dean McDermott

Tori Spelling and Dean McDermott Disney On Ice

 (Photo: SIPA / WENN.com)

Now this is how we’d expect a home-wrecking marriage to be going! Dean and Tori were both married to other people (Dean to Mary Jo Eustace, Tori to Charlie Shanian) when they first met on the set of the Lifetime movie Mind Over Matter, but still began their affair that very night. The two of them got married in 2006, a month after Tori’s divorce was finalized, and had been together ever since…until Dean cheated on Tori with a Canadian rando earlier this year. But guys. Seriously. Are we shocked? I’m more surprised by the fact that they made it eight years together without that happening sooner.

4. Melanie Griffith and Antonio Banderas

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 (Photo: Dennis Van Tine / Future Image / WENN.com)

Yeah, so these two just separated, but before that, they were married for eighteen years! That’s a serious run for a pairing that started out with Melanie cheating on her husband Don Johnson with Antonio, who was simultaneously cheating on his wife Ana Leza. Both got divorced in 1996 and married each other in the same year, aka they had basically zero downtime. I don’t know how they held it together for as long as they did.

5. Woody Allen and Soon-Yi Previn

Woody Allen and Soon-Yi Previn To Rome With Love Premiere

(Photo: WENN.com)

Ugh, don’t even get me started on these two. If you believe Woody’s version of events, Soon-Yi was over eighteen before he started pursuing her, and he was never really a father figure to her, even though she was the adopted daughter of his partner, Mia Farrow. I strongly disagree there, but regardless, one thing everyone agrees on is that Woody got involved with Soon-Yi while he was still with Mia. Only makes it more creepy that they’ve been married since 1997, seventeen years. Gross.

6. Ryan Philippe and Abbie Cornish

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(Photo: Getty Images)

Ryan was still married to Reese Witherspoon when he and Abbie met on the set of Stop-Loss in 2007, and considering that their relationship is rumored to have ended Ryan and Reese’s marriage, it’s surprising to me that Abbie and Ryan lasted another three years together before ultimately breaking up in 2010.

7. Jesse James and Kat Von D

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 (Photo: WENN.com)

Based on the fact that Kat was just one of many women whom Jesse was accused of cheating on his then-wife Sandra Bullock with prior to their divorce in 2010, I’m surprised anyone would want anything to do with him ever again. But Kat did, getting engaged to him in 2011, only to break up with him later that year, get back together, and break up for good in September 2011, accusing Jesse of cheating on her mutliple times during their relationship and engagement. OF COURSE HE DID, MAYBE DON’T GET ENGAGED TO THAT GUY.

8. Meg Ryan and Russell Crowe

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(Photo: Getty Images)

Did you guys know this? Meg Ryan and Dennis Quaid had been married for nine years when she hooked up with Russell Crowe on the set of Proof of Life in 2000. They only lasted a couple months as a couple after Meg and Dennis’ divorce, but that’s a pretty long time given the circumstances! How does that happen??

9. Angelina Jolie and Billy Bob Thornton

Angelina Jolie and Billy Bob Thornton attending premiere of Tomb Raider July 2001

 (Photo: WENN.com)

Welcome back to the list, Miss Jolie! How nice to see you again! This is yet another relationship that I wasn’t aware of, but apparently Billy Bob was engaged to Laura Dern when he first met Angelina on the set of Pushing Tin. Laura Dern has said that she went off to work on a project, and when she came back, her fiance was married to another woman:

“I left home to work on a movie, and while I was away, my boyfriend got married, and I’ve never heard from him again.”

Said marriage only lasted from 2000 to 2003, but that’s a surprisingly decent run, considering.

So…good job I guess, guys? You impressed me, but that’s not hard to do when you yourselves set the bar so low. If you gotta cheat, just cheat once.

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  • Ash

    Don’t forget Julia Roberts and her husband, Danny Moder. If I remember correctly, she was still with Benjamin Bratt and he was married when they met on The Mexican.

    • Alexis Rhiannon

      Oh nice! Good memory!

    • Lena

      And Julia was such an asshole about it. She went around wearing a t-shirt that said, “A Low Vera,” (Vera is Danny’s ex’s name) while the divorce was being finalized.

  • Elizabeth Aspen

    Pretty slimy of you to say there was cheating between Brad and Angie. Brad has stated that his marriage was already on the rocks when they met and even Courtney Cox said in Vanity Fair that Brad didn’t cheat – he went to Jennifer and said he was attracted to Angie, but nothing happened. That’s what an honorable man does – goes to his wife and is straight up with her before anything physical happened. Not many men would do that. Marriage isn’t a forever thing, and anyone who goes into it thinking ‘this is the one I’ll be with forever’ is a fool. Brad fell in love with someone else who wanted exactly what he wanted, and he would have been a moron to stay in a marriage to nowhere.

    • Alexis Rhiannon

      I definitely agree with you, which is why I made a point to say that they both insist nothing physical happened. But it’s undeniable that Brad was married at the time. You’re right that he did the correct thing, which was to go to Jennifer right away, but the fact that a relationship had to end for them to be together is why he’s on this list.

    • just me

      I’m certain marriage is supposed to be a ‘forever thing’ and that’s why vows say ’til death do us part’ and not ‘until i grow and evolve and hopefully that’s with you.’

  • Cheeta

    Sorry, but with the Crowe/Ryan thing, it started because DENNIS QUAID cheated on Ryan for several years during the late nineties. Their marriage was over and she was no longer living with him, when she hooked up with Crowe.
    Funny how a serial cheater like Quaid always gets a pass from the gossippages. Just ask his current third wife. She’s had to live with his cheating ways for years too. Only reason she stays with him is his $$$

  • Mockingjay

    I don’t actually think Kat Von D was involved with Jesse while he was married to Sandra and cheating with the other ladies. I think they got together some time after.I believe it was after he went to rehab and she thought he changed I believe but I could be wrong

    • Jen TheTit Whipper

      I think you’re correct, or at least that’s what transpired legally.

  • Jen TheTit Whipper

    Cheating sucks. But sometimes decent relationships come out of it. And while yes it happened, I get more annoyed that it’s brought up repeatedly. Like in every interview. You can’t discuss Brad/Angelina or Eddie/LeAnn without it being brought up. Yet everyone has moved on, except us, I guess.

    • Alexis Rhiannon

      Yeah, you’re right. I think I mostly wanted to write this because I always forget how long-lasting couples started, and it’s sometimes interesting to remember that they started with infidelity. It’s definitely not the most important or even interesting part of a relationship, just curious.

    • Jen TheTit Whipper

      I liked the article. I think it is interesting to kinda look back. But I’d venture to guess if you ever interviewed Brad/Angie you wouldn’t be asking about Jennifer Aniston.

    • Alexis Rhiannon

      Oh god no. I’d ask what to name my kid if I ever have one, because they crush it with the names.

  • Kate

    Missing Tom Hanks and Rita Wilson…a couple so cute I’m willing to overlook that Tom cheated on his college sweetheart.

    • Alexis Rhiannon

      Oh my god, I had no idea!

  • Lena

    Does anyone else remember all the rumors about how shaky Brad and Jennifer’s marriage was long before Angelina was in the picture? Did my brain just make that up? I could have sworn that things were not going well for them for a while, with Aniston saying a whole lot of weird things about marriage and relationships that had me speculating.

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