15 of the Most Bitter Hollywood Breakups

Where Did the Love Go? 15 of the Most Bitter Hollywood Breakups

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Hollywood relationships are often fleeting, but as we’ve seen time and time again they are also volatile. A loving relationship can go sour with the speed of Internet. The celebs on this list went from Love to War while the whole world got to watch. Take a look at some of the most bitter Hollywood breakups.

Justin and Britney


Photo: WENN

The Justin and Britney split was perhaps the most shocking and publicized  breakup in recent Hollywood history. The world thought these two young love birds would spend their lives together but with rumors of  Britney cheating on Justin in 2002 with either Wade Robson or Ben Affleck (we’re not sure which), it was clear that would not happen. Justin was so hurt he took to blasting Brit in his famous “Cry Me A River,” which essentially confirms rumors of her infidelity. He even had a Britney look-a-like in the video. Britney was shamed for her actions and hurt by the whole situation, and fell into a downward spiral.

 Halle Berry and Gabriel Aubry

Halle and Gabriel WENN pf

Photo: WENN.com

We’re not sure what exactly caused the split between these two but what once appeared to be an amicable breakup turned into a  narsty custody fight over their 4-year old daughter Nahla. Since dating Oliver Martinez, Halle has been trying to take Nahla to France where they would live once Halle and Oliver wed, but ex Gabriel wasn’t having it. Halle lost that fight. The battle turned ugly on Thanksgiving 2012 when Gabriel and Oliver got into fists-to-cuffs over the whole situation.

 Liza Minnelli and David Gest

Liza Minnelli and David Gest WENN pf

Photo: WENN

This marriage was a flash in the pan. Liza and David had a hugely extravagant wedding complete with legends like Michael Jackson and Elizabeth Taylor. It was even televised but the couple separated a year later. There was even a lawsuit by Gest claiming Minnelli had been a violent alcoholic and abusive towards him while Liza claimed David was just after her money.

 Usher Raymond and Tameka Foster 


Photo: Judy Eddy / WENN

Usher and ex-wife Tameka Foster went through a very public custody battle over their 2 sons following their 2009 divorce after being married just two years. Usher accused his ex of being inattentive, irresponsible, and unstable while Tameka claimed Usher was a cheating, absentee father that abused drugs. In the end, Usher was awarded full custody of the kids as Tameka was left grieving over her recently deceased 11-year old son from a previous relationship. There was even reports that Usher put the house Tameka was living in up for sale. Talk about kicking someone while they’re down.

Alec Baldwin and Kim Basinger

Alec Baldwin and Kim Basinger

Alec Baldwin and Kim Basinger were married for nine years, resulting in one daughter. The circumstances of the divorce are up for guessing, but one thing is for sure, they had a  n*sty custody battle that went on for 7 years as a result. Kim was hellbent on keeping Alec away from daughter Ireland. Baldwin claims that she denied him communication to their daughter, would disregard court orders, and would directly try to turn her against him, but he blames her attorneys more than anything (he even admitted to wanting to murder her counsel). The entire battle cost them each $1 million dollars and was punctuated by an angry voicemail in 2007 in which Alec called his daughter a “rude thoughtless little pig.”

 Kelsey and Camille Grammer

Kelsey and Camille Grammar WENN pf

Photo: Joseph Marzullo/Wenn.com

Camille Grammer filed for divorce from husband of 13 years, Kelsey Grammer, in July 2010 while she was a cast member on the Real Housewives of Beverly Hills. Just one month later it was revealed that Kelsey had been having an affair with a British flight attendant named Kayte. Kelsey and Camille’s divorce turned vitriolic.  In 2012 Kelsey took to publicly bashing his marriage to Camille, telling Oprah “it was over pretty much as soon as it began” and admitting to Conan O’ Brien that they hadn’t had sex in a decade! He even described their marriage as a “self-imposed prison sentence.”

Charlie Sheen and Denise Richards

Charlie Sheen and Denise Richards WENN pf

Photo: WENN

Richards filed for divorce from Sheen in 2006, alleging that the actor was unstable, violent, addicted to gambling and prostitutes, and into p0rn0graphic websites featuring what appeared to be underage girls. She also claimed Sheen assaulted her and threatened to kill her in 2005. She even got a restraining order against him. What followed was a custody battle over Charlie’s rights to the children, accusations that Denise was after more of his s p e r m for a 3rd child, accusations of lying by both parties which included Sheen’s then new wife Brooke Mueller, and a failed attempt by Sheen to keep his children off of Denise’s reality show It’s Complicated.

 Heather Mills and Paul McCartney

Paul McCartney and Heather Mills WENN pf

Photo: Jody Cortes/WENN

McCartney and Mills had a 6 year marriage that turned into a bitter divorce after the fourth year. Mills claimed McCartney was a boring drunk who cruelly hid her prosthetic leg and forced her to crawl to the bathroom at times. The media criticized Mills saying that she only married The Beatles legend for his money. When their 2 year divorce battle was over McCartney said, “There’ll be no more nagging, no more chaos, no more Heather … bliss. I have peace at last”

 Sienna Miller and Jude Law

Jude Law and Sienna Miller WENN pf

Photo: Andres Otero/WENN.com

When news of Jude Law’s infidelity to his fiancé Sienna Miller was reported in July 2005 by no one other than the woman he cheated with, their relationship was as good as dead. The nanny of Jude’s children went public with the news after one of Jude’s children caught them in bed together and told the mother, actress Sadie Frost, who then relieved the nanny of her job. Miller broke off her engagement to Law, and the two broke up. Interestingly, they have since rekindled their romance and broken up again.

Seal and Heidi Klum

Heidi Klum and Seal WENN pf

Photo: FayesVision/WENN.com

These to looked like the picture of happiness together with their 4 children, so when they split it was a bit of a surprise. Klum filed for divorce in April 2012 after almost 7 years of marriage. The split was amicable up until Seal told TMZ that he wished Heidi had “at least waited until they separated first before deciding to with the help, as it were.” His statement was in reference to Klum’s then new relationship with her body guard while the couple was separated though still legally married.

Mel Gibson and  Oksana Grigorieva

Mel Gibson and  Oksana Grigorieva WENN pf

Photo: Sean Thorton/WENN.com

Mel Gibson’s ex and mother of his youngest child filed for a restraining order against him in June 2010 a few months after the couple split. Mel filed a restraining order against her just days later in retaliation. Oksana also contended that Mel had been violent towards her, leading to a domestic violence investigation. During that time some recordings of Mel spewing very rac1st, sexist, and abusive remarks towards her leaked to the media.

 Demi Moore and Ashton Kutcher

Demi Moore and Ashton Kutcher WENN pf

Photo: Apega/WENN.com

Demi and Ashton divorced amid rumors that Ashton had been unfaithful. Prior to the divorce the couple had been dogged by rumors of Ashton cheating which they both denied in a round about way. The couple remained together, but in November 2011 Moore released a statement saying “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. ” Sounds like someone broke his vows…

  Sandra Bullock and Jesse James

Sandra Bullock and Jesse James WENN pf

Photo: Apega/WENN.com

Amid the continuing headlines of Tiger Woods’ infidelity scandal came news that Sandra Bullock’s hubby Jesse James had cheated on her, too. Several women came forward claiming they had affairs with James during his 5-year marriage to Bullock. He issued a public apology to his wife and entered sex rehab in hopes of salvaging his marriage, but a month later Sandra filed for divorce and later adopted by herself the child the two had planned to adopt together.

 Evelyn Lozada and Chad Johnson 


You could see early on during Basketball Wives when Evelyn started dating Chad Johnson that the relationship was premature and doomed to fail, but how the relationship ended was a pretty big twist. Just one month into their marriage Chad headbutted Evelyn during an argument, leaving him kicked off the Dolphins football team with a domestic battery charge and a swift divorce.

Kim Kardashian and Kris Humphries

"Kim and chris"

Photo: WENN

This couple had a highly publicized 72-day marriage that had the whole world feeling duped. Kim filed for divorce on October 31, 2011. Humphries filed his response requesting an annulment on the grounds of fraud. The couple is still married, though, Kim is trying her darnedest to get Humphries to sign off on the divorce since she’s expecting her first child with beau Kanye West.

  • S. Owzarek

    Did you pass your English class Cassie. It said into their marriage. “Their” is spelt correct.

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