Heartbreak is never easy. Some of Hollywood’s biggest names in music, movies and TV have suffered unpleasant splits over the years, from Britney Spears and Justin Timberlake to Rihanna and Chris Brown to Taylor Swift and Calvin Harris. Take a look back with Us Weekly at the most bitter celebrity breakups of all time.
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Heartbreak is never easy. Some of Hollywood’s biggest names in music, movies and TV have suffered unpleasant splits over the years, from Britney Spears and Justin Timberlake to Rihanna and Chris Brown to Taylor Swift and Calvin Harris. Take a look back with Us Weekly at the most bitter celebrity breakups of all time.
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The “Shake It Off” singer and “We Found Love” DJ split in June 2016 after 15 months together. Less than two weeks later, she was photographed kissing Tom Hiddleston on a beach near her Rhode Island mansion. Shortly after the pics surfaced, Harris unfollowed Swift on social media and then tweeted and deleted, “Oh boy it’s about to go down.” In the following weeks, she went on a PDA-filled adventure with Hiddleston across the globe, traveling everywhere from England to Italy.
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After dating on and off for nearly a decade, the Keeping Up With the Kardashians stars officially called it quits on their relationship in July 2015 after he was spotted getting a little too close with his ex-girlfriend Chloe Bartoli. Kardashian and Disick first started dating in 2006 and are parents of Mason, Penelope and Reign.
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The Two and a Half Men alum and his fiancée called off their engagement in October 2014. More than a year later, Rossi filed a lawsuit against Sheen alleging assault and battery, emotional distress, false imprisonment and negligence. In April 2016, she was granted a temporary restraining order against the HIV-positive actor, who, at present, is reportedly under criminal investigation by the LAPD as of July 2016. Sheen has since filed for a dismissal of Rossi’s claims.
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The R&B singers split in September 2014 after three years together. Derulo later admitted that he called it quits over the phone, while Sparks revealed that she returned the BMW he gifted her and told him to “come get your s--t" following their messy breakup. In May 2015, he told Billboard magazine, “I do get tired of playing nice. Especially when people think I did something wrong, or that she broke up with me. But it’s so behind me.”
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The “Love Yourself” crooner and “Good for You” songstress dated on and off from 2011 to 2014. Following their split, both have opened up on multiple occasions about their tumultuous relationship. In February 2016, Gomez told W magazine of her history with Bieber, “I’m so exhausted. … I honestly am so done. I care about his health and well-being. But I can’t do it anymore.”
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The Barbadian beauty and “Back to Sleep” hitmaker’s tumultuous relationship made headlines in February 2009 after he assaulted her in a car the night before she was scheduled to perform at the 51st Grammy Awards. In June 2009, Brown pleaded guilty to felony assault. Three years later, in 2012, the couple briefly rekindled their romance (and recorded the duet “Birthday Cake” together) before splitting again in 2013. Rihanna told Vanity Fair in a November 2015 cover story that she “was very protective” of Brown and felt that she could change him. “But you know, you realize after a while that in that situation you’re the enemy … They know you don’t deserve what they’re going to give,” she said.
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Us Weekly exclusively revealed in July 2012 that the Twilight actress cheated on her costar boyfriend with her Snow White and the Huntsman director, Rupert Sanders. The pair struggled to repair the damage caused by the fling and ultimately called it quits in May 2013. In April 2015, Pattinson proposed to singer FKA Twigs after six months of dating.
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The daughter of politician Sarah Palin and the former Playgirl model ended their engagement in March 2009, just three months after they welcomed their first child, Tripp. The pair battled each other in an Alaskan court in a bitter seven-year custody case, which ultimately ended in the judge ruling in favor of Johnston in February 2016. In June 2016, Bristol tied the knot with Dakota Meyer, the father of her second child, Sailor.
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The Bachelor season 14 star shocked fans when he dropped to one knee and proposed to villainess Girardi in the March 2010 season finale. The pair broke off their engagement in June 2010 and got into a heated screaming match during a July 2010 live Bachelor special, which ended in Girardi walking out in tears, yelling, “He is the biggest liar I’ve ever met in my life!” The reality stars later starred together in ABC’s spin-off series Bachelor Pad 2.
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The Mean Girls actress and DJ dated on and off from 2008 to March 2009. In November 2012, Lohan recounted the rocky romance in an exclusive interview with Us Weekly, explaining, “I was bold enough to say, ‘Yeah, I like a girl. And?’ That put her in a situation where she was being attacked every day. That’s not fair. And what am I left with? Heartbreak. … I needed to love myself before I could be with anyone. And I was going through a lot. Two toxic people cannot be together. End of story.” In April 2016, the actress and tabloid fixture got engaged to Russian business heir Egor Tarabasov.
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After seven months together, the heiress and Backstreet Boys singer ended their relationship in July 2004. Carter later revealed that neither of them trusted each other. In his 2013 autobiography, he wrote, “Paris was the worst person in the world for me to hook up with. [She] fed my worst impulses as far as partying.” In April 2014, the singer tied the knot with his longtime girlfriend Lauren Kitt. They welcomed their first child, son Odin Reign, in April 2016.
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The hitmakers met in the early '90s while working on a revival of The Mickey Mouse Club. They started dating circa 1999 and went on to become pop royalty in the early aughts. Spears and Timberlake split in 2002 amid rumors that she cheated on him. (Speculation grew even more intense when he featured a Spears look-alike in his “Cry Me a River” music video.) Since then, the “Toxic” songstress has had two children, Sean Preston and Jayden James, and two failed marriages, to childhood pal Jason Alexander and dancer Kevin Federline. Timberlake — who revealed in a 2011 interview with Vanity Fair that he hadn’t spoken to Spears in “nine or 10 years” — married Jessica Biel in October 2012 and welcomed son Silas in April 2015.
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