Random Most Tragic Celebrity Breakup Stories (19 items)

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  (#20) Britney Spears

  • Band/Musician

  We kind of knew this relationship was headed for disaster. But it was so much fun to watch, especially when B. Spears and K. Fed put their relationship on display for their TV show Britney & Kevin: Chaotic. After allegations of infidelity on his part, she let him know she was divorcing him via text message.
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  (#16) Rihanna

  • Band/Musician

  Even after he beat her up, Rihanna intially decided to stay with Chris Brown. The two have been on and off again since the 2009 incident. But as the singer later told Diane Sawyer, “When I realized that my selfish decision for love could result into some young girl getting [slain], I could not be easy with that part. I couldn’t be responsible … If Chris never hit me again, who’s to say that their boyfriend won’t … [slay] these girls.” 
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  (#12) Anne Hathaway

  • Actor

  Hathaway and Follieri split in 2008 after the Italian businessman was convicted of defrauding investors out of millions of dollars. In an interview with ABC News, Follieri had this to say: "She was very sweet to me. We had, I think, a very nice relationship. I don't have anything bad to say."
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  (#9) Amy Poehler

  • Comedian

  It sounds like scheduling was the main reason behind Amy Poehler and Nick Kroll's divorce. “Unfortunately, they just couldn’t make the relationship work with their schedules,” a source told Inquistr. 
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  (#5) Blake Shelton

  • Band/Musician

  Country music's star couple divorced in July 2015, much to the dismay of fans. While it seems that things just fell apart for the couple, the rumor-mill was swirling with allegations that The Voice star had gotten close with his co-star Gwen Stefani, who was also going through a divorce from rocker Gavin Rossdale.
  
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  (#11) Selena Gomez

  • Band/Musician

  Will we ever know the true story of what happened between Justin and Selena? After breaking up and making up numerous times, the two officially split in 2014. As she told Glamour magazine in September 2015, "It's all part of my story. I'm growing and changing. I was in a relationship, and I was being managed by my parents, and I was still under Hollywood and Disney, and I was being held to this expectation of being the good girl."

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