The 20 Most Savage Celebrity Breakups Of All Time

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It sucks being dumped no matter what the circumstances, but spare a thought for these 20 celebrities. They all learned that their relationships had come to an end via the most impersonal, inappropriate and just plain mean ways ever. And they’ll make you realize that dating and marrying in Tinseltown definitely isn’t all it’s cracked up to be…

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20. Katy Perry and Russell Brand

In 2011 Katy Perry and Russell Brand became the poster children for how not to do breakups. That’s because on the penultimate day of that year Brand sent a text message to Perry telling her he was divorcing her after just over a year of marriage. Unsurprisingly, they didn’t stay friends.

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19. Laura Dern and Billy Bob Thornton

Jennifer Aniston may not like Angelina Jolie much, but chances are Laura Dern doesn’t either. Why? Well, Angie was the woman her fiancé Billy Bob Thornton abandoned her for. “I left our home to work on a movie, and while I was away my boyfriend got married and I’ve never heard from him again,” Dern told Talk magazine. Ouch.

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18. Adam Levine and Jessica Simpson

Jessica Simpson’s relationship with Maroon 5 singer Adam Levine in the mid ’00s did not end remotely well. In fact, he reportedly ended it with just four words sent by text. They were these: “Really busy. Need space.” He could have at least put a little more effort into it.

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17. Kiefer Sutherland and Julia Roberts

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In 1991 Julia Roberts ditched her engagement with Dylan McDermott in order to instead get engaged to Kiefer Sutherland – and it was a disaster. Such a disaster, in fact, that she called the wedding off three days before it would’ve happened. And she didn’t tell Sutherland herself but got a friend to do it. No wonder she ended up starring in Runaway Bride

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16. Taylor Swift and Joe Jonas

In 2008 Taylor Swift revealed on The Ellen DeGeneres Show just how her teenage relationship with fellow singer Joe Jonas had come to an end. And it wasn’t pretty. He had broken up with her via a phone call that had lasted a mere 27 seconds. Yikes.

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15. Sylvester Stallone and Jennifer Flavin

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Sylvester Stallone isn’t known for being a sweet talker, but when he split up with model Jennifer Flavin in 1994, he sent her a six-page letter via FedEx. Naturally, she wasn’t pleased in the slightest. It wasn’t all over for the couple, though. They eventually reconciled and, in 1997, got married.

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14. Jason Derulo and Jordin Sparks

Jason Derulo actually admitted to ditching Jordin Sparks in one of the harshest possible ways. In a 2014 radio interview on New York’s Power 105.1, the singer admitted that he’d dumped her “over the phone… I wasn’t in town.” What, he couldn’t have waited?!

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13. Heather Locklear and Richie Sambora

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Poor Richie Sambora. When his wife Heather Locklear filed for divorce, she somehow neglected to tell him. So when a reporter asked the touring rocker if things were all right at home, he responded in the affirmative and talked about how happy he would be to see her for Valentine’s Day. Ouch.

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12. Jarret Stoll and Rachel Hunter

Hockey player Jarret Stoll of the Los Angeles Kings broke off his wedding to model Rachel Hunter in the worst possible way. He emailed her, two months before it was due to happen, to tell her it was off! Hunter, who had already thrown herself into wedding preparations, was devastated.

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11. Jennifer Lopez and Ben Affleck

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When “Bennifer” finally came to an end, it was with a whimper rather than with a bang. Somewhat shamefully, Ben Affleck called off his wedding to Jennifer Lopez just a few days before it was due to happen. “I don’t think I had ever been heartbroken in that way before,” Lopez told Behind the Music in 2010.

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10. Ariana Grande and Jai Brooks

In a 2013 interview with Complex magazine, Ariana Grande talked about her worst ever breakup. “The worst way I’ve been broken up with was probably over a text message the opening night of my tour right before I was about to go on stage,” she said. And it didn’t take the internet long to identify the culprit: her one-time boyfriend Jai Brooks.

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9. Kevin Federline and Shar Jackson

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Before he became known as Britney’s beau, Kevin Federline was partner to actress Shar Jackson. But when he met the pop princess, he ditched Jackson… while she was pregnant with their second child. And while Federline did eventually apologize to her on a 2010 episode of Celebrity Fit Club, it may very well have been a case of too little, too late.

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8. Hugh Hefner and Crystal Harris

Hugh Hefner, Playboy tycoon – unlucky in love? Yep. In 2011 his would-be wife Crystal Harris called off the wedding just five days before the event, leaving Hefner to sadly tweet, “The wedding is off. Crystal has had a change of heart.” But eventually she changed her mind and married him in 2012.

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7. Porsha Williams and Kordell Stewart

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TV personality Porsha Williams had an absolute nightmare of a breakup. One quiet day in 2013, she woke up from a nap, went onto Twitter… and found out that her husband Kordell Stewart was divorcing her. And he was sitting in the next room. She marched through to confront him, but she’s never revealed exactly what was said. However, it probably wasn’t nice.

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6. Billy Crudup and Mary-Louise Parker

Billy Crudup pulled the ultimate betrayal in 2003 when he left his seven-months-pregnant long-term partner Mary-Louise Parker for a younger model, Claire Danes. Needless to say, Crudup and Danes received large amounts of backlash. “I was just in love with him,” Danes said in a 2015 Howard Stern interview. “I didn’t quite know what those consequences would be.”

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5. Clint Eastwood and Sondra Locke

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Clint Eastwood may have once been a heartthrob, but based on past behavior, he isn’t the sort of person you would actually want to get romantically involved with. For example, once his relationship with his long-time partner and co-star Sondra Locke came to an end in April 1989, he simply changed the locks and moved her stuff out while she was away. Harsh.

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4. Kesha Ni’Cole Nichols and Richard Jefferson

Dancer Kesha Ni’Cole Nichols had her 2009 wedding to NBA star Richard Jefferson canceled via email – the night before! Though she told Good Morning America a week after the fact that she “wasn’t in shock” when she received it, it’s still a remarkably impersonal way to end a relationship.

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3. Tiki Barber and Ginny Cha

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It’s a special kind of brutal to ditch your wife and the mother of your children while she’s eight months pregnant with twins. But that’s exactly what footballer Tiki Barber did to his wife Ginny, running off as he did with a pinup model who had previously pretended to be a babysitter. Then to make matters worse, he compared his having to lie low after the media fallout to Anne Frank having to hide from Nazis. Bad move, dude.

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2. Kevin Federline and Britney Spears

For Kevin Federline, what went around came around. After ditching Shar Jackson for Britney Spears, he became the ditchee – live on camera, no less – when Spears sent him a text message saying that their two-year marriage was over. And the fallout was incredibly painful.

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1. Matt Damon and Minnie Driver

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One of the most infamous public ditchings of all time came at the hands of Matt Damon when he appeared on Oprah in 1998. He was asked if he and girlfriend Minnie Driver were still a couple, and he said no – which was news to Driver. Later, she bitterly described his actions to the L.A. Times as “fantastically inappropriate.”

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