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Hollywood romances don't always have a fairy-tale ending. Some of the most famous, rich and beautiful pairings just weren't able to go the distance and became better known for their toxic uncouplings than their once-happy unions. Join us as we take a look at the messiest celeb breakups — starting with this split, which has given the world a brand new album, "Chemistry," which drops on June 23, 2023…

Fans can hear all about Kelly Clarkson's messy roller-coaster split from husband and manager Brandon Blackstock on her 2023 album, "Chemistry." Kelly filed for divorce in June 2020 after nearly seven years of marriage and within months, the breakup battle had exploded amid numerous court hearings involving money and property. Brandon demanded the singer and talk show host — who won primary custody of their two kids, with visitation for their father one weekend a month — pay him a jaw-dropping $436,000 a month in spousal and child support. He eventually ended up with $160,601 — but only until January 2024 — plus a one-time payment of more than $1.3 million.

Aside from contentious support issues, their Montana ranch became a battleground. Though Kelly was awarded ownership, per their prenup, Brandon was living on the property at the time, which saw her attempt to evict him. She lost that fight and ultimately had to give him 5.12% of the ranch ($908,000 of its $17,750,000 value). Nearly two years after Kelly filed, they settled the divorce in March 2022. "I don't know how people get through anything like that because I'm not going to say I did it gracefully. Behind closed doors by myself, it was no," Kelly admitted to Apple Music's Zane Lowe of their traumatic split. 

Keep reading for more of the most traumatic celebrity breakups of all time…

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Angelina Jolie and Brad Pitt famously fell for each other while filming 2005's "Mr. & Mrs. Smith" — while he was still married to Jennifer Aniston. They wed in 2014 but split two years later when she suddenly filed for divorce and asked for sole custody of their six kids — Maddox, Pax, Zahara, Shiloh and twins Vivienne and Knox — citing "the health of her family." An altercation on a private plane sparked an abuse investigation into Brad's behavior (he was cleared by authorities) and the Oscar winners have been battling it out in court ever since over everything from custody to how Angelina handled the sale of her share of their French chateau. As of 2023, the pair reportedly had not yet finalized a financial settlement even though a judge declared them legally single in 2019. Angelina told British Vogue in February 2021 that after the bitter split, "I've been focusing on healing our family. It's slowly coming back, like the ice melting and the blood returning to my body."

MORE: Notorious celebrity cheating scandals

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Before Brangelina, Brad Pitt and Jennifer Aniston were Hollywood's golden couple. The pair wed on a cliff in Malibu in 2000 but split almost five years later. The "Friends" star called her ex out for "a sensitivity chip that's missing" after he posed with new flame Angelina Jolie for a 60-page W magazine feature titled "Domestic Bliss" in March 2005, the same month Jen filed for divorce amid whispers that Brad had cheated with his "Mr. & Mrs. Smith" co-star. In 2011, Brad reflected on his first marriage, telling Parade he got "sick of myself sitting on a couch, holding a joint, hiding out. It started feeling pathetic… I wasn't living an interesting life. I think that my marriage had something to do with it. Trying to pretend the marriage was something that it wasn't."

MORE: Celebrity couples with big age gaps

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Johnny Depp and Amber Heard met on the set of the 2011 film "The Rum Diary," announced they were an item in 2012 and married in February 2015. But after 15 months, they split — and it quickly became one of the ugliest celebrity divorces in history, with graphic allegations of physical and emotional abuse flying from both sides. The former couple ended up rehashing their toxic marriage in court when Johnny sued a U.K. tabloid for libel after it referred to him as a "wife beater" in print. In November 2020, he lost when a British judge ruled that the words were "substantially true." He was denied permission to appeal the verdict but the "Pirates of the Caribbean" star maintained his innocence and insisted that Amber was the abusive one. In 2022, Johnny's won a defamation suit he filed against Amber over a 2019 opinion essay she published in The Washington Post in which she said she'd become a "public figure representing domestic abuse." he was awarded $10.4 million.

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After 14 years of marriage, Ioan Gruffudd and Alice Evans split in March 2021. Things quickly turned nuclear seven months later when Ioan made it Instagram official with his new love, actress Bianca Wallace. Alice, who has two daughters with the "Fantastic Four" actor, went on numerous Twitter rants accusing him of cheating and abandoning their family including one that read, "So it turns out that my husband, after two years of telling me I'm a bad person and I'm not exciting and he no longer want so to have sex with me and he just wants to be on set abroad… Has been in a relationship for THREE years behind all our backs. Good luck, Bianca."

Things continued to get worse and in 2022, Ioan filed a petition for a domestic violence restraining order against his ex. Then in 2023, their older daughter, Ella, filed for a restraining order against her father and a civil harassment protection from his girlfriend.

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Sandra Bullock was riding high after an Oscar win for "The Blind Side" in February 2010 when she was blindsided by news that her husband of five years, Jesse James, had cheated on her with a tattoo model. More women soon came forward claiming they had affairs with the "Monster Garage" star, and in April of that year, Sandra filed for divorce — and announced she and Jesse had been in the process of adopting a baby boy. She continued the adoption as a single mother while Jesse released a statement saying, "My whole life has been full of hard decisions. The decision to let my wife end our marriage, and continue the adoption of Louis on her own, has been the hardest."

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Russell Brand ended his 14-month marriage to Katy Perry in 2011 by texting her the news that he was divorcing her. The singer has hinted about the reason for the split, telling Vogue, "I felt a lot of responsibility for it ending, but then I found out the real truth, which I can't necessarily disclose because I keep it locked in my safe for a rainy day." The English comedian, meanwhile, said in his 2015 documentary "Brand: A Second Coming" that the relationship was doomed because in marrying the "Roar" singer, "I'm associated with the very thing I detest: vapid, vacuous, plastic, constructed, mindless celebrity."

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After a whirlwind romance, Tom Cruise and Katie Holmes welcomed daughter Suri in April 2006 and seven months later tied the knot at a star-studded wedding in an Italian castle. Their divorce announcement in 2012 shocked fans — as did revelations that Katie blindsided Tom by using a disposable phone and lawyers in multiple states to file for divorce without him knowing she wanted out. At the time, the "Dawson's Creek" alum's publicist released a statement saying, "Katie's primary concern remains, as it always has been, her daughter's best interest." Despite speculation that Katie ended the marriage to remove herself and her daughter from Tom's Scientology community, the stars have never publicly discussed the reason for the divorce.

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After Nicole Kidman and Tom Cruise split in 2001 after 10 years of marriage and two kids, there was no shortage of fallout. People magazine reported that Tom cryptically told people that "Nicole knows why" the marriage ended. Nicole — who suffered a miscarriage not long after Tom left her — has maintained she doesn't know why the "Mission Impossible" star filed for divorce and had "thought our life together was perfect," she later told DuJour magazine. But she was photographed looking ecstatic leaving her divorce lawyer's office on the day their split was finalized. She later joked to late night host David Letterman, who asked how she felt about the split, "Well, I can wear heels now."

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NFL icon Tom Brady and actress Bridget Moynahan met in 2004 and dated for just over two years before splitting in 2006. The star quarterback began dating his now-wife, supermodel Gisele Bundchen, shortly after the breakup — and within weeks, Bridget revealed she was pregnant with her ex's child. The pregnancy, surprise split and Tom's high-profile new romance put Bridget in the spotlight during an already-traumatic time. "I would have cars following me, and men hiding in the bushes outside my house," she later told People magazine. "As a new mother, you want to just protect your child. That kind of attention felt like a threat."

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Mary-Louise Parker and Billy Crudup's seemingly solid romance went terribly awry when he left his partner of eight years — who was seven months pregnant with their son at the time — for his "Stage Beauty" co-star Claire Danes. The "Weeds" actress never directly addressed the split publicly. But in her 2015 memoir "Dear Mr. You," she referenced the breakup's aftermath in a letter she penned to a cab driver who had gotten lost while driving the then-pregnant star to a doctor's appointment. Stressed out, she began to swear at the driver, who stopped and asked her to stop shouting. When she continued, the driver asked her to get out, telling her, "I don't want you anymore." Mary-Louise replied, "No one does," telling him, "My life is worse than yours in this moment… I am pregnant and alone. It hurts to even breathe."

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Tiger Woods was the world's best golfer, married to Swedish former model and nanny Elin Nordegren, and father to two healthy children, when his life exploded in 2009. The athlete's infidelity was exposed, leading to a late night Thanksgiving bust-up with Elin, who chased him from their Florida home with a golf club before he crashed his Escalade. By the time the dust settled, Tiger had checked into a rehab facility for sex addiction and dozens of women had come forward to claim they had affairs with him while he was married. He and Elin finalized their divorce in August 2010 and have co-parented daughter Sam and son Charlie ever since.

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Halle Berry and Eric Benet were happily married until news broke in 2002 that he was cheating on her. He had admitted to sleeping with 10 other women in their short three years of marriage, including with two of her close friends. "We all know I cheated. It was out there. It's a betrayal," the R&B singer told People magazine in 2005. Halle later revealed she tried to repair the marriage but had an "emotional breakdown" when she learned the extent of Eric's affairs. He entered rehab for sex addiction, but the pair split in 2003.

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Woody Allen and Mia Farrow never legally married, but their breakup after 12 years together was one of the most talked about, and toxic, in show business history. In 1992 Mia discovered photos of her eldest adopted daughter, Soon-Yi Previn, without clothing in Woody's apartment. The director later testified that his intimate relationship with Soon-Yi began in late 1991 when she was a 21-year-old college freshman and he was 56. Several months after she discovered the scandalous photos, Mia accused Woody of molesting their young daughter Dylan, charges both women maintain are true but which he has vigorously denied and which have never resulted in legal charges. Soon-Yi and Woody married in 1997 and are now parents to two adopted daughters.

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Shania Twain and husband Robert "Mutt" Lange split in 2008 after 14 years of marriage amid an epic scandal: He was allegedly cheating with her close friend and longtime manager of the couple's Swiss chateau, Marie-Anne Thiébaud. The country superstar and the reclusive music producer 17 years her senior married in 1993 just six months after they met and soon welcomed a son. Though Shania was devastated by Mutt's betrayal, the story had the happiest of endings for the singer: She fell in love with Marie-Anne's husband, Frédéric Thiébaud, and they went on to marry on New Year's Day in 2011. "I'm so grateful I found the faith and courage to love again," Shania told People magazine in February 2020. "Because the last thing you want to do when you're crushed is love again."

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Kristen Stewart and Robert Pattinson made "Twilight" fans' dreams come true when they coupled in real life. Their breakup three years later was as dramatic as could be: Kristen was caught on camera cheating on Rob with her married "Snow White and the Huntsman" director, Rupert Sanders. Despite reuniting briefly after the scandal, the duo were done for good by 2013.

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For his lavish $3 million proposal to Kim Kardashian, Kanye West rented out San Francisco's AT&T Park, brought a blindfolded Kim onto a dark baseball field where a 50-piece orchestra serenaded her with her favorite Lana Del Rey song, got down on one knee and presented her with a 15-carat Lorraine Schwartz diamond ring while the scoreboard flashed "PLEEEASE MARRY MEEE!!!" She did, but after welcoming daughters North and Chicago and sons Saint and Psalm with the rapper-fashion designer, Kim ended their relationship by filing for divorce in February 2021. The SKIMS founder moved on with "Saturday Night Live" star Pete Davidson in late 2021. But even though Ye has been dating other women — including artist-actress Julia Fox — he didn't let go easily, repeatedly making public comments about wanting to save his marriage and shading Pete in his song "Eazy" (with lyrics like: "God saved me from that crash / Just so I can beat Pete Davidson's a**") — before shifting to publicly criticizing Kim's parenting. Kim and Kanye's divorce was ultimately finalized in November 2022.

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Gwen Stefani and Gavin Rossdale had been together for 20 years, married for 13 and were doting parents of three boys when it all came crashing down in 2015. The No Doubt singer split with the Bush frontman amid a nanny cheating scandal — according to Us Weekly, Gwen found out about the affair when another nanny discovered intimate photos and texts on the family's iPad. Silver-lining alert: Healing from the traumatic split brought Gwen close to her fellow "The Voice" judge Blake Shelton, who was suffering through his own nasty breakup from music star Miranda Lambert, and they married in 2021 after five years as a couple.

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Blake Shelton and Miranda Lambert were country music royalty when they suddenly split in 2015 after four years of marriage and a decade together. An Oklahoma judge granted their divorce just two weeks after Blake filed, which only added to the traumatic nature of their breakup, which was surrounded by rumors and allegations of infidelity on both sides. When asked if his song "She's Got a Way with Words" — about a lover who lied and cheated — referred to his ex, Blake told Billboard, "When we recorded the vocals for some of these songs, I was only six months removed from when all the crap went down. When you have a broken heart — at least, when I do — you got to get it out of your system. You want people to sympathize with you. I was at rock bottom, in the middle of hell."

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While Laura Dern was away from home shooting a movie, fiancé Billy Bob Thornton ghosted her… and married Angelina Jolie behind her back. "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," she told Talk magazine in 2000. "It's like a sudden death. For no one has there been any closure or clarity."

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Demi Moore and Ashton Kutcher seemed to defy the odds with their unlikely romance. The couple, who had a 15-year age gap, wed in 2005. He was a doting stepfather to her three daughters with ex-husband Bruce Willis. The couple renewed their vows in 2010. But after a magazine accused Ashton of cheating with a 23-year-old on his sixth wedding anniversary, they hit the skids and split in 2013 after eight years of marriage. Demi detailed their tumultuous relationship, including allegations of infidelity and threesomes, in her 2019 memoir "Inside Out." The pair are now friendly and Ashton maintains a relationship with his former stepdaughters. "I make a really conscious effort to stay in touch with the girls," he revealed in 2020 on Marc Maron's podcast. "I loved them and I'm never gonna stop loving them and respecting them and honoring them and rooting for them to be successful in whatever they're pursuing."

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After years of on-and-off dating, Khloe Kardashian and Tristan Thompson split (again) in June 2021. Despite his multiple cheating scandals over the years, Khloe had always seemed willing to try to make things work with the NBA player, with whom she shares daughter True. But that all changed in January 2022 when Tristan publicly confirmed he'd fathered a baby with another woman a month earlier. "Khloe, you don't deserve this," Tristan wrote in an Instagram Story on Jan. 3. "You don't deserve the heartache and humiliation I have caused you. You don't deserve the way I have treated you over the years. My actions certainly have not lined up with the way I view you. I have the utmost respect and love for you. Regardless of what you may think. Again, I am so incredibly sorry." Making things even more difficult? Khloe and Tristan had moved forward with having a second child together, son Tatum, via surrogate — who was impregnated right before Tristan's mistress gave birth.

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Remember the OG Bennifer? Jennifer Lopez and Ben Affleck got engaged in 2002 — the same year he starred in her 2002 "Jenny From the Block" video — but they postponed their September 2003 wedding a day before it was supposed to take place. In January 2004, J.Lo called off the whole relationship, and five months later, she married Marc Anthony. Ben, who went on to have three kids with Jennifer Garner, has said media scrutiny "was about 50%" to blame for their split, explaining to radio host Howard Stern in December 2021, "The idea that people hate you and they hate you together and that being together is poison and ugly and toxic." Of course there's a sweet ending to this split story: J.Lo and Ben reunited 17 years later in 2021 and married in 2022.

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Ben Affleck and Jennifer Garner fell for each other while shooting the 2002 movie "Daredevil" while both had significant others (he was engaged to Jennifer Lopez, she was married to Scott Foley). By 2005, they were married and expecting a baby. But one decade and three children later, they dropped the bomb that they were splitting and weeks later, reports claimed Ben had been hooking up with their nanny. "We had been separated for months before I ever heard about the nanny. She had nothing to do with our decision to divorce. She was not a part of the equation," Jen later told Vanity Fair. "Bad judgment? Yes. It's not great for your kids for [a nanny] to disappear from their lives. I have had to have conversations [with my children] about the meaning of scandal." After an ugly three-year-long breakup, their divorce was finalized in October 2018.

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Justin Bieber and Selena Gomez started dating as teens and were on and off for nearly eight tumultuous years before ending things for good in 2018. The pair never officially commented on rumors of Justin's infidelity — but in 2016, they got into a spat in the comments section of one of his Instagram posts, with Selena heavily hinting that the rumors were true: "Funny how the ones that cheated multiple times, are the ones pointing the finger at the ones that were forgiving and supportive," she wrote. In 2019, Justin's alleged infidelities were front and center again when Selena released her breakup hit "Look at Her Now," which featured the lyrics: "They fell in love one summer / A little too wild for each other / Shiny till it wasn't / Feels good till it doesn't / It was her first real lover / His too till he had another / Oh god, when she found out / Trust levels went way down."

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Of all Taylor Swift's breakups, her parting with Calvin Harris after 15 months together was especially bitter. When Tay started dating British actor Tom Hiddleston weeks later, the DJ and music producer went on a Twitter rant calling out her songwriting pseudonym, Nils Sjoberg, on his hit track "This Is What You Came For" — and in the feud that followed he called out the pop star's penchant for public fights. "I know you're off tour and you need someone new to try and bury like Katy [Perry] ETC but I'm not that guy, sorry. I won't allow it," he wrote. "Please focus on the positive aspects of YOUR life because you've earned a great one. God bless everyone have a beautiful day."

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Britney Spears and Justin Timberlake were childhood sweethearts whose romance bloomed as their fame grew. They split in 2002 amid rumors that Britney cheated on Justin with choreographer Wade Robson. Five months after their breakup, JT told Barbara Walters that he would always love Britney and had "promised" her he would never discuss the details of their split. But many believe his 2002 hit "Cry Me a River" — whose video featured him revenge-cheating on a Britney look-alike — was about the end of their relationship: "I thought our love was so strong / I guess I was dead wrong / But to look at it positively, hey girl / At least you gave me another song about a horrible woman."

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When Miley Cyrus and Liam Hemsworth tied the knot in 2018, it seemed like they'd put their rocky relationship history behind them. The couple had broken up more than once since meeting on the set of 2010's "The Last Song," but in 2015 they got together and three years later they made it official. Yet in August 2019, less than eight months after they married at Miley's Tennessee home, the duo announced their separation. Miley quickly moved on with MTV reality star Kaitlynn Carter and then with singer Cody Simpson. The exes have shaded each other multiple times, including in an October 2019 livestream when Miley claimed that Cody was the only "good guy" she has dated.