The Most Bitter Celebrity Breakups

March 25, 2015  |  
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Love can be a beautiful thing, but when relationships end, sometimes bitterness trumps all the other feelings. These celebrity couples went from being in love to duking it out in public.

Floyd Mayweather and Shantel Jackson

Floyd “Money” Mayweather is undefeated in the boxing ring, but he has been very unlucky in love. The boxing champ was with Shantel Jackson for seven years and the two were even engaged before calling it quits early last year. Following their split, they both took public shots at each other: Mayweather posted a sonogram on Instagram and claimed he broke up with Jackson because she aborted their twins; Jackson took a jab of her own and held a press conference to announce her lawsuit against him, claiming Mayweather physically assaulted her on several occasions and threatened to shoot her in the foot.

Usher Raymond and Tameka Raymond

Usher’s mother was proven right when his marriage to Tameka Foster (now Raymond) ended in disaster. They squared off in court in a bitter custody battle, with the “Confessions” singer claiming that his ex-wife was inattentive, unstable and irresponsible, and she called him an absentee dad who abused drugs and cheated with one of her bridesmaids. After their case dragged out in court and in the media, Usher was eventually awarded full custody of their two young sons.

Kim Kardashian and Kris Humphries

Kim Kardshian will go down in history as having one of the shortest marriages in Hollywood. Her union with NBA baller Kris Humphries lasted a mere 72 days before she decided to call it quits. But Humphries was hurt to no end and alleged that he was duped into thinking their relationship was real when she was actually faking it all along for the cameras. Humphries originally filed a petition to have their marriage annulled on the grounds of fraud, and he dragged his feet when it came to the divorce proceedings. Two years later, their divorce was finalized. Twelve days after that, Kardashian gave birth to Kanye West’s child.

Khloe Kardashian and Lamar Odom

Kim isn’t the only Kardashian who’s been through a bitter breakup. Khloe Kardashian met NBA star Lamar Odom and a month later they were running down the aisle towards holy matrimony. Even though she was initially desperate to have his baby, she soon realized that their marriage was doomed and wanted out. Odom’s career stalled after his alleged drug abuse spiraled out of control, and his rumored infidelity didn’t help these two go their separate ways in peace. They still haven’t officially finalized their divorce.

Big Sean and Naya Rivera

Big Sean and Naya Rivera met on Twitter in 2013, and soon they took things offline and into the real world. They were so smitten with each other that the “Marvin & Chardonnay” rapper popped the question a few months later. But after a year of being together, they called it quits. Reportedly, he wasn’t too keen on the “Glee” star’s controlling ways. During couples therapy he realized how unhappy he was in their relationship.
Although Big Sean wished her well, she accused him of stealing back the Rolex watch he gave her. The rapper denied such claims, and in retaliation, he dropped “IDFWU.”

Halle Berry and Gabriel Aubry

After two failed marriages, Halle Berry thought she found love again with Canadian model Gabriel Aubry. But after welcoming their daughter, Nahla, into the world, their relationship fell apart. The two squared off in court over custody of Nahla because Berry wanted to move with her to France. There was also a fight for support, which Aubry currently receives ($16,000 a month). Speaking of things Aubry has received, he also was on the receiving end of a beatdown at the hands of Berry’s then-boyfriend, Olivier Martinez.

Eva Longoria and Tony Parker

Eva Longoria and Tony Parker made the cutest celebrity couple–that is until Longoria and the rest of us found out about his cheating ways. The San Antonio Spurs point guard was allegedly sleeping around with his teammate’s estranged wife (Brent and Erin Barry were going through a divorce of their own around the same time). Even though they signed a prenup, it was amended two years into their marriage and Longoria sought spousal support. Their divorce was finalized in 2011. The pint-sized actress and producer admitted to being depressed following their breakup.

Heidi Klum and Seal

Seal and Heidi Klum were so in love with each other that they renewed their wedding vows each year–that is until they announced their split after seven years of marriage. The “Kiss From A Rose” singer went on to claim that Klum was sleeping with the “help” before they separated. Though Klum denied even looking at another man during their marriage, she did begin a relationship with the family’s bodyguard, which Seal obviously wasn’t too happy about.

Justin Timberlake and Britney Spears

JT and Britney Spears were the ultimate “it” couple back when they dated from 1999-2002. but a young Timberlake was devastated when he found out that Spears was creeping behind his back. He used his heartbreak to provide us with “Cry Me A River.” The music video even included a Spears look-alike, and the song helped launch Timberlake as a successful solo artist.

Demi Moore and Ashton Kutcher

You know a woman is scorned when she wants to take your money even though she has more than enough money of her own. Demi Moore was one of Hollywood’s most infamous cougars after she married Ashton Kutcher. Sadly, she decided to call it quits after he allegedly spent their sixth wedding anniversary with other women. Her statement following their split hinted at such infidelity:

“As a woman, a mother, and a wife, there are certain values and vows that I hold sacred, and it is in this spirit that I have chosen to move forward with my life.”

It took two years for their divorce to be finalized because the G.I. Jane star wanted spousal support and a piece of Ashton’s Two and a Half Men money.

Kelsey and Camille Grammer

While Camille Grammer was making her debut on the Real Housewives of Beverly Hills, her husband, Kelsey, was spending time in New York, starring on Broadway. And oh yeah, he was spending time falling in love with another woman. Kelsey met and fell for flight attendant Kayte Walsh. When Camille found out, the two put on their boxing gloves and duked it out in divorce court–and in the media. The Frasier star trashed their marriage of more than a decade, saying it was over as soon as it began. He even claimed they hadn’t had sex in 10 years. Two weeks after their divorce was finalized, Kelsey married Walsh.

Paul McCartney and Heather Mills

Paul McCartney was beyond devastated when he lost his wife Linda after her battle with cancer. But he was able to find love again with model Heather Mills. Or so he thought.

Their six-year marriage turned ugly towards the end and things got even uglier when they announced that they were divorcing. Mills went to the media and said the famous Beatle was a drunk who hid her prosthetic leg and forced her to crawl around the house. After separating in 2006, they were finally free and clear of each other by 2008 when their divorce was finalized. McCartney exclaimed, “There’ll be no more nagging, no more chaos, no more Heather — bliss. I have peace at last.”

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