22 Messy Celebrity Breakups That Were Hard to Watch

Celia San Miguel | Aug 25, 2016 Celebrities
22 Messy Celebrity Breakups That Were Hard to Watch

As the saying goes, breaking up is hard to do. But when you're a celebrity couple under constant media scrutiny, parting ways is that much tougher. Infidelities, substance abuse issues, custody battles, and bitter arguments all tend to become public knowledge, making the experience all the more emotionally taxing and humiliating. Oftentimes, the parties involved only add salt to the wound by airing their own dirty laundry, badmouthing their exes or making thinly veiled accusations.

From Amber Heard and Johnny Depp's acrimonious divorce to the Angelina Jolie cheating scandal that ended Jennifer Aniston's marriage to Brad Pitt, here are some of Hollywood's messiest and most cringeworthy breakups. 


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  • Halle Berry & Gabriel Aubry

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    When these two beautiful people broke up, they were left with one hot mess! In early 2010, Halle Berry and model Gabriel Aubry parted ways after five years, agreeing to split custody of their daughter Nahla, then 2 years old. Things got heated, however, after Berry became engaged to actor Olivier Martinez in 2012 and asked a family court judge for permission to move to her fiancé's native France with Nahla. Berry's petition was denied that November, and a judge ordered that a shared custody arrangement be established. Weeks later, Martinez and Aubry wound up in a bloody brawl over the ongoing custody battle. The exes are still in court over child support fees, with the Oscar winner fighting to reduce he $16,000/month payments she makes to her baby daddy.

  • Katy Perry & Russell Brand

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    After 14 months of marriage, comedian Russell Brand informed pop superstar Katy Perry that he wanted a divorce — via text message. Talk about bad breakup etiquette! The two reportedly haven't spoken since the Textgate incident in December 2011, but they've certainly taken jabs at each in the media. In a 2015 documentary, Brand said he split from Perry after realizing he was "living this life of the very thing I detest: vapid, vacuous celebrity." Perry, meanwhile, suggested that Brand was threatened by her success. "He didn't like the atmosphere of me being the boss on tour," she said in Vogue's July 2013 issue. "That was really hurtful, and it was very controlling, which was upsetting." 

  • Chris Brown & Karrueche Tran

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    During the course of their tumultuous relationship, Karrueche Tran and Chris Brown broke up at least three times. But Tran got a real gut punch when, in March 2015, she learned via TMZ that Chris Brown had fathered a child with another woman: model Nia Guzman. He'd not only cheated on her, but he'd managed to conceal the existence of a 9-month-old baby! Feeling betrayed, humiliated, and heartbroken, Tran gave Brown the ultimate kiss-off via Twitter, writing, "One can only take so much. The best of luck to Chris and his family. No baby drama for me." CB tried to patch things up, but there was no salvaging that relationship.

  • Kim Kardashian & Kris Humphries

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    In October 2011, after 72 days of marriage to basketball player Kris Humphries, reality TV star Kim Kardashian filed for divorce. According to reports, Humphries found out his new wife planned to end their marriage after reading about it on TMZ. By December, Humphries filed a motion to have his marriage to Kim Kardashian annulled, claiming their nuptials were a fraud designed to boost KUWTK ratings. Both parties' lawyers claimed the opposite side was stalling the proceedings. The divorce wasn't finalized until April 2013, when Kardashian was 7 months pregnant with North West. 

    More from CafeMom: 15 Biggest Celebrity Breakups of 2016 -- So Far

  • Charlie Sheen & Denise Richards

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    In March 2005, while six months pregnant, Denise Richards filed for divorce from Charlie Sheen, her husband of five years, claiming he was abusing drugs, had serious anger management issues, and was a gambling addict. A bitter divorce and custody battle over their two daughters followed. In April 2006, Richards was granted a restraining order against her ex mandating he stay at least 300 yards away from her and the girls, except during supervised visits. The two seemed to establish a truce in 2009 but, by 2015, Sheen was up to his old tricks, going on a Twitter rant and calling Richards the "worst mom alive" and "an evil terrorist." You're sooo not #winning, Charlie!

  • Heidi Klum & Seal

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    The world was shocked when, in January 2012, Heidi Klum and Seal announced they were divorcing after seven years of marriage — after all, theirs seemed like a fairy-tale romance, replete with lavish yearly vow renewal ceremonies. The split soon turned ugly, with Seal accusing Klum of having an affair with her bodyguard prior to their separation. "Whilst I didn't expect anything better from him, I would've thought that Heidi would have shown a little more class and at least waited until we separated first before deciding to fornicate with the help," Seal told TMZ. Klum scoffed at the allegations, saying she never even looked at another man while with Seal. In 2014, their divorce was finalized.

  • Paula Patton & Robin Thicke

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    R. Kelly got one thing right: When a woman's fed up, there ain't nothing you can do about it. In February 2014, actress Paula Patton separated from Robin Thicke, her husband of nine years. The reason behind their split was the source of much conjecture, with most reports alleging that he'd been unfaithful. The "Blurred Lines" singer was desperate to win back his high school sweetheart, releasing the highly personal tune "Get Her Back," naming his confessional 2014 album Paula, and dedicating his song "Forever Love" to his estranged wife at the 2014 BET Awards. The grand overtures were majorly cringeworthy and, in the end, futile: Patton filed for divorce in October 2014.

  • Johnny Depp & Amber Heard

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    Though divorce rumors plagued Amber Heard and Johnny Depp since their February 2015 nuptials, nobody could've predicted how acrimonious their split would actually be. Heard filed for divorce in May 2016 and immediately asked for a restraining order, alleging that Depp had verbally and physically abused her during their 15-month marriage. Depp's camp worked overtime to dismiss Heard as a lying opportunist who was capitalizing on the lack of a prenup. She, however, had plenty of ammo: In August, she leaked a cell phone video in which a visibly intoxicated Depp could be seen shouting, slamming cabinet doors, and throwing wine glasses. On August 15, TMZ published a story detailing how Depp cut off his fingertip during a fit of rage and dipped his bloody digit in blue paint, writing "Billy Bob" and "Easy Amber" on a mirror (he suspected Heard of cheating with her former costar Billy Bob Thornton). The day after the TMZ piece, Depp and Heard reached a divorce settlement and she vowed to donate her $7 million cut to charity. 

    More from CafeMom: 15 Celebrity Couples Plagued by Breakup Rumors

  • Tom Cruise & Nicole Kidman

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    Throughout the '90s, Nicole Kidman and Tom Cruise were Hollywood's ultimate power couple — the precursors to Brangelina and Bey-Z. Then, in February 2001, Cruise filed for divorce, citing "irreconcilable differences" — which not only shocked audiences, but blindsided Kidman herself. She responded to his divorce petition via court papers, claiming his decision came out of nowhere and that, upon discovering his desire to separate, she'd begged him to stay and seek marriage counseling, which he refused. Kidman also claimed she'd suffered a miscarriage as a result of the stress over her marital woes. In the end, they were granted a divorce and Kidman lost custody of their two adopted children, Isabella and Connor. Recent reports claim that the Church of Scientology drove a wedge between Kidman and Cruise and brainwashed the kids against their mom.

  • Taylor Swift & Calvin Harris

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    After celebrating her 1-year anniversary with Calvin Harris, it seemed like Taylor Swift had finally found a guy she wouldn't wind up writing an angst-ridden song about. Then, on June 1, People confirmed the couple had split. The breakup seemed drama-free and amicable — that is, until two weeks later, when photos emerged of Taylor Swift kissing actor Tom Hiddleston. As #Hiddleswift went public, Harris responded with thinly veiled jabs at his ex, releasing the breakup track "Olé," which includes the lyrics, "I see online that you've begun to be a good girl and take trips with your boyfriend, being attentive / Continue to pretend." In July, when Swift revealed she had penned Harris's song "This Is What You Came For" using a pseudonym, the DJ/producer was enraged, taking to Twitter to vent his frustration and claiming she was attempting to tarnish his image.

  • Tiger Woods & Elin Nordegren

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    If the rumors are true, Tiger Woods's ex-wife Elin Nordegren is pretty handy with a golf club. After hearing whispers of her husband's indiscretions, a suspicious Nordegren scoured through her husband's cell phone contacts and text messages. On Thanksgiving 2009, she discovered some incriminating texts from a New York City nighclub hostess and went berserk, allegedly chasing him out of the house with a golf club and smashing the rear windows of his Escalade as he attempted to flee. Nordegren eventually walked away with a hefty divorce settlement and custody of the kids. 

  • Sandra Bullock & Jesse James

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    On March 7, 2010, Sandra Bullock accepted her Best Actress Oscar for The Blind Side as her husband of five years, TV personality and motorcycle guru Jesse James, looked on. A week later, tabloids began publishing stories alleging that Jesse James had been cheating on Bullock with tattooed model Michelle "Bombshell" McGee for almost a year. By late March, James publicly acknowledged his infidelities, apologized to his wife, and begged for her forgiveness. Bullock decided to end the marriage, filing for divorce. While she showed grace and poise during a difficult time, we felt mortified for her as more mistresses came out of the woodwork.

    More from CafeMom: The Saddest Celebrity Breakups Ever 

  • Demi Moore & Ashton Kutcher

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    Demi Moore unwittingly popularized the term "cougar" when she hooked up with Ashton Kutcher, who was 15 years her junior. Despite all the raised eyebrows, the couple, who wed in 2005, seemed blissful. Then, in October 2011, a 22-year-old woman named Sara Leal came forward, claiming she'd had a one-night stand with Ashton Kutcher in a San Diego hotel room. After announcing the end of her marriage in November, Moore seemed to unravel, losing an alarming amount of weight, winding up in the ER after a seizure caused by inhaling nitrous oxide, and ultimately checking herself into rehab. The Ghost star then went from sad to mad: When Kutcher officially filed for divorce in December 2012, she responded by demanding spousal support. She eventually withdrew the request and, in November 2013, they became free agents. 

  • Mariah Carey & Nick Cannon

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    On December 12, 2014, Nick Cannon filed for divorce from Mariah Carey, his wife of six years and the mother of his then-3-year-old twins, Monroe and Moroccan. But, even before he took to the courthouse, Cannon was airing the couple's dirty laundry, admitting in August 2014 that there was "trouble in paradise" and saying they had been living in separate homes for months. Then came the infidelity rumors when, that October, Mariah performed Billie Holiday's "Don't Explain" and changed a lyric to "I know you cheated, motherf***er." Yikes! As the turmoil continued and news of the impending divorce broke, a visibly heartbroken Mariah began breaking down during concerts. She eventually moved on and is now engaged to James Packer, but she's still waiting for Nick to sign the divorce papers. 

  • Reese Witherspoon & Ryan Phillippe

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    Reese Witherspoon was only 24 when she married Ryan Phillippe back in 1999, but the Cruel Intentions costars managed to make it through seven years together (a lifetime in Tinseltown!) and bring two beautiful kids into the world: Ava and Deacon. In 2006, however, the baby-faced spouses announced they were separating. Allegedly, Reese had found a text message on Ryan's cell phone confirming her suspicions that he'd been having an affair with his Stop Loss costar Abbie Cornish. Though neither party confirmed the rumors, the fact that Phillippe dated Cornish for the next four years seemed like proof enough!

  • Robert Pattinson & Kristen Stewart

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    Twilight costars Kristen Stewart and Robert Pattinson were the poster children for millennial love — until, that is, paparazzi photographed Stewart making out with her Snow White and the Huntsman director, Rupert Sanders, in July 2012. By the end of the month, Stewart was apologizing for her "momentary indiscretion" and pleading for fans' forgiveness, all the while professing her love for Rob. The pair eventually reconciled but the cheating scandal remained in the tabloids, making it hard for either of them to move past the betrayal. By May 2013, Pattinson moved out of their shared pad. The trust between them had clearly been broken.

    More from CafeMom: 10 Celebrities Who Regret Their Breakup With An Ex

  • Jennifer Garner & Ben Affleck

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    On June 30, 2015, one day after their 10-year wedding anniversary, Ben Affleck and Jennifer Garner announced they were splitting up. Within a month's time, they found themselves at the center of a media hurricane, as rumors swirled that Affleck had been sleeping with Christine Ouzonian, his kids' nanny. The claim was supported by a paparazzi shot of her arriving to a late-night meetup with the Argo actor driving his Lexus, a champagne bottle in hand. A year later, tabloids claim Garner is unsure about whether or not to move forward with the divorce. The humiliation of having her hubby frolicking with the nanny — and of having the attention-seeking Ouzonian flaunting the fling — surely can't make it an easy decision!

  • Usher & Tameka Foster

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    Maybe Usher should've heeded his mom's advice. Usher's mother was so opposed to his marrying stylist Tameka Foster that she was a no-show at his nuptials. Usher fans were similarly disapproving, pegging Tameka as a gold digger, cradle robber, and manipulative opportunist. To no one's surprise, Usher filed for divorce in November 2009. They initially agreed to share custody of their children — Usher "Cinco" and Naviyd Ely — but, in 2012, Foster filed a motion to regain full custody of the boys. A vicious battle ensued during which Tameka's lawyers claimed he prioritized partying over parenting and Usher's attorneys claimed Tameka had spit on the singer's new girlfriend, Grace Miguel. In September 2012, the courtroom circus concluded when Usher was granted full custody.

  • Alec Bladwin & Kim Basinger

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    Two years after costarring in 1991's The Marrying Man, Alec Baldwin and Kim Basinger tied the knot. Behind closed doors, however, Kim says life with Alec Baldwin mirrored Sleeping With the EnemyAllegedly fed up with Baldwin's explosive temper, Basinger filed for divorce in 2001. Alec struck back at the rage monster portrayals of him in the media, claiming Kim was mentally unhinged and that she interpreted "all dissent as abuse." Their nasty and highly publicized divorce raged on for years as they fought over custody of their daughter Ireland. Then, in 2007, a voicemail was leaked to the press in which an irate Alec referred to his daughter as a "rude, thoughtless little pig." Eventually, Alec lost the custody battle, but he did make peace with his daughter and, eventually, with his ex.

  • Brad Pitt & Jennifer Aniston

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    In January 2005, Brad Pitt and Jennifer Aniston announced they were separating after five years of marriage. At the time, they dismissed all tabloid rumors as false -- particularly those about Pitt cavorting with his Mr. & Mrs. Smith costar Angelina Jolie. In the wake of the separation, however, Pitt was constantly photographed alongside Jolie — even as the two continued to deny their affair. Some tabloids blamed Aniston for the demise of her marriage to Pitt, claiming she refused to give him children and was obsessed with her career. By July 2005, Pitt and Jolie were posing together for W magazine as the ultimate family in a "Domestic Bliss" spread. Aniston replied to the spread by saying Pitt lacked "a sensitivity chip." Sure enough, in January 2006, three months after Pitt's divorce was finalized, Angelina announced she was pregnant.

    More from CafeMom: 8 Most Shocking Celebrity Rebounds

  • Britney Spears & Kevin Federline

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    Everyone except Britney Spears, it seems, knew Kevin Federline was trouble. The "Oops! I Did it Again" singer married the bad boy backup dancer in September 2004 and filed for divorce in November 2006, less than two months after the birth of their second child, Jayden James, and asked for sole custody of the kids. K-Fed found out about Britney's divorce motion via text message and responded by filing his own motion for sole custody. Britney began partying too hard, checking in and out of rehab, driving without a license, and behaving bizarrely. Though the divorce was finalized in March 2007, the custody battle was only beginning. Federline was granted primary sole custody in October 2007, and Britney didn't regain shared custody until 2011.

  • Ciara & Future

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    As Ciara graced on the cover of Brides magazine's August/September 2014 issue, her relationship with her fiancé Future was imploding. Rumors surfaced that the "Bugatti" rapper had cheated only three months after Ciara gave birth to their son Future Jr. Despite a brief attempt at reconciliation, by December, they'd parted ways. Though Ciara moved on to date (and eventually marry) football star Russell Wilson, Future continued talking about his ex in a less-than-flattering manner. In January 2016, Future went on a Ciara-bashing Twitter rampage, claiming she was making it too difficult for him to see his child, tweeting, "This b*tch got control problems." Ciara is currently suing him for libel and defamation.

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