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Celebrities Who Broke Up with Their BFFs

Updated January 2, 2020 614.0k views17 items

BFF stands for "Best Friends Forever" – until it doesn't. For this list of celebrities who broke up with their BFFs, the letters might as well stand for "Broken Friendship Files." These famous actors, comedians, and musicians all broke up with their celebrity BFFs, many after years-long relationships. Some celebrity ex-friends parted ways due to creative differences while other celebrity friend breakups stemmed from complicated love triangles.

In the tabloid era, the most famous set of best friends who broke up is likely Paris Hilton and Lindsay Lohan. In the mid-2000s, the two starlets seemed like a perfect match. But in 2006, it became clear that the former besties were on the outs when the ladies launched a war of words in clubs and in the media. And they aren't the only famous women on the list. For a period of time Gwyneth Paltrow and Madonna were inseparable. By 2010, it was obvious who Paltrow was referring to when she said, "I'm having a situation right now with a friend where I'm feeling pretty angry."

BFF breakups aren't just for the ladies. Before he was Ari Gold on Entourage, Jeremy Piven was best known for playing John Cusack's friend in just about every movie from the 1980s. The actors became buddies growing up in Chicago, but they broke up when Piven felt resentment from Cusack due to his recent success.

What other famous ex-friends make the list? Keep scrolling to find out.
  • In the mid-2000s it seemed like Paris Hilton and Lindsay Lohan were a BFF match made in heaven. Unfortunately, their friendship didn't last long – by 2006, the starlets were lobbing insults at each other in clubs and the media.
    • Age: 39
    • Birthplace: New York City, New York, United States of America

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  • In 2015, Taylor Swift alluded to her now non-existent friendship with fellow pop singer Katy Perry. "If you betray your friend, if you will talk about them badly behind their back, if you will try to humiliate them or talk down to them, I have no interest in having a person like that in my life," she said.
    • Age: 30
    • Birthplace: Reading, Pennsylvania, United States of America

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  • Paul Simon & Art Garfunkel
    Photo: Joost Evers / Wikimedia Commons / CC BY-SA 3.0 NL
    Paul Simon and Art Garfunkel made beautiful music together, but Garfunkel was burned by his bandmate when Simon walked away from their success in 1970. "I don’t want to say any anti Paul Simon things, but it seems very perverse to not enjoy the glory and walk away," said Garfunkel.
    • Age: 78
    • Birthplace: Forest Hills, New York City, New York, United States of America

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  • For a period of time Gwyneth Paltrow and Madonna were inseparable, and it's unclear what ultimately caused their split. Whatever the reason, by 2010, Paltrow was not-so-subtly making statements like, "I'm having a situation right now with a friend where I'm feeling pretty angry."
    • Age: 48
    • Birthplace: Los Angeles, California, United States of America

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