Top 10 Messiest Celebrity Breakups

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Top 10 Messiest Celebrity Breakups

VOICE OVER: Phoebe de Jeu WRITTEN BY: Tal Fox
We're still not over the messiest celebrity breakups. Our countdown includes Britney Spears & Justin Timberlake, Kristen Stewart & Robert Pattinson, Johnny Depp & Amber Heard, and more!
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Top 10 Messiest Celebrity Breakups


Welcome to MsMojo, and today we’re counting down our picks for the Top 10 Messiest Celebrity Breakups

For this list, we’ll be looking at celebrity couples whose separations were far from amicable.

Which celebrity split surprised you the most? Let us know in the comments!

#10: Britney Spears & Justin Timberlake


Let us head back to the very early 2000s, when Britney and Justin rocked the double denim look together, and gave us all relationship envy. But then in 2002, we learned that our favorite pop couple had broken up, and everyone wanted to know why. Rumors started flying that the pop princess had cheated on her beau with choreographer Wade Robson but the only insight we had was JT’s song “Cry Me a River” which only fueled our speculations. However, since Justin vowed to never reveal the reason behind the split, this is one breakup that will forever remain a mystery.

#9: Sandra Bullock & Jesse James


After winning the Oscar for Best Actress for “The Blind Side,” news broke that after five years of marriage, Bullock had been blindsided by her then-husband’s infidelity. Several women came forward confessing to flings with Jesse James, leaving the actress heartbroken. Although he made a public apology and checked into rehab, the damage had been done. and she filed for divorce. The couple was also in the process of adoption procedures during this time, which Bullock continued alone. In 2017, James divulged to the MailOnline that he had “no regrets” about his actions and that cheating is just “a part of life”.

#8: Angelina Jolie & Brad Pitt


Despite its rocky beginnings, “Brangelina” quickly became one of Hollywood’s golden couples, and we were sure it was forever. However, in 2016, after more than a decade together, six children, and a secret wedding in 2014, the couple announced their separation. Jolie cited her children's well-being as the reason for their split but a lengthy custody battle ensued, with Jolie asking for full custody while only granting Pitt visitation rights. This didn’t sit well with the actor, who took the case to court. Jolie also accused the media of vilifying her throughout the process which probably didn’t help the already hostile atmosphere.

#7: Kanye West & Amber Rose


Before officially becoming “Kimye”, Kanye’s then-girlfriend, Amber Rose accused the pair of hooking up while she and Kanye were together. She alleged that Kim instigated the relationship by sending pictures and even went as far as labeling her a “homewrecker,” while insisting that Kanye could never be faithful. In defense of his wife, Kanye responded by slut-shaming his ex and saying that he needed “30 showers” before he could be with Kim. The feud didn’t stop there with even Khloe jumping in to defend her sister on Twitter, while everyone involved essentially continued to fight for the last word.

#6: Kristen Stewart & Robert Pattinson


After months of speculating, “Twihards” were thrilled to learn that Kristen Stewart and Robert Pattinson were a real-life item. While they tried hard to keep their relationship out of the spotlight, they shot straight into headlines when Kristen was spotted cozying up to the married director, Rupert Sanders, while shooting “Snow White and The Huntsman”. A source denied that it was anything more than a “fleeting moment” and a “bad choice” and the actress even made a public apology. While the couple initially tried to work past it, it seemed like the trust was gone, and soon after they called it quits.

#5: Demi Lovato & Max Ehrich


This whirlwind relationship went public in March 2020, with the happy couple announcing their engagement in July… shortly followed by their split in September. While lockdown may have accelerated the relationship, Demi hit the brakes when she started questioning Max’s intentions. and ultimately decided to try to erase evidence of the relationship. Meanwhile, Max took a more vocal approach through his Instagram Stories, even claiming that he only learned of the breakup through tabloids and he was even snapped returning to the scene of the proposal. Demi is clearly after a clean break, and we hope Max is able to get one too.

#4: Kim Kardashian & Kris Humphries


This marriage famously lasted only 72 days before Kim filed for divorce from NBA player Kris Humphries. While both insist they were in love, many, including Kris, speculated that the wedding had been a publicity stunt to boost ratings for Kim’s reality TV career, and he even tried to file for annulment on those grounds. As we mentioned earlier, rumors of “Kimye’s” fling were rife too. The divorce lasted much longer than the relationship, with both sides blaming the other for the constant delays. In fact, by the time the divorce was finalized, Kim was already heavily pregnant with North.

#3: Johnny Depp & Amber Heard


As well as being an understatement of “messy,” this breakup is deeply concerning for all involved. Initially meeting on the set of “The Rum Diary” their later marriage only lasted a year with Heard filing for a restraining order, after alleging that Depp had been physically abusive. After the divorce was finalized, Depp sued British newspaper, “The Sun” for libel after they called him a “wife beater,” putting the spotlight back on their toxic relationship. During this trial, plenty of other incredibly disturbing and worrying claims were brought to the surface, highlighting how twisted and troubled their relationship actually was.

#2: Tiger Woods & Elin Nordegren


One of the major stories of 2009 revealed that Tiger Woods had been cheating on his wife with many women. It was rumoured that Woods knew the story was about to break and tried to reassure her that it wasn’t true, but Elin had her doubts and found all the proof she needed on his phone. Supposedly, she woke her sleeping husband and chased him out the house with his clubs, and then actually smashed the window of his car. While Elin eventually walked away with a substantial settlement, Woods learned that he should have kept his golf club in its bag.

Before we unveil our top pick, here are a few honorable mentions.

Eminem & Kim Mathers
This Couple Actually Divorced Twice, and Have You Heard His Song “Kim”? Yikes!

Kate & Jon Gosselin
Fame Brought Out the Ugly Side of This Relationship

Heather Mills & Paul McCartney
Plenty of Explosive Moments Emerged From This Divorce

Demi Moore & Ashton Kutcher
Rumours Surfaced About Kutcher’s Infidelity

Taylor Swift & Calvin Harris
The Music Producer Took to Social Media After This Breakup

#1: Jennifer Aniston & Brad Pitt


After five years, this marriage became “The One with the Rumor” that Brad Pitt had been getting very close to his “Mr. & Mrs. Smith” co-star (and we already saw how that ended). This ugly breakup was very public, with unavoidable photos of the new relationship everywhere, while Jen admitted she was hurt by media coverage which detailed how Brangelina fell in love during her marriage. The media also pitted the women against each other, asking the public if they were “Team Jennifer” or “Team Angelina”. Despite all the unpleasantness, they’ve put the past behind them and now insist that there is nothing more between them than friendship.
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