Hollywood

Most Memorable Breakups in Hollywood History

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BRAD PITT AND JENNIFER ANISTON
BRAD PITT AND JENNIFER ANISTON

Brad and Jen: Could there BE a more attractive couple? Well, after Brad met Angelina Jolie while filming Mr. & Mrs. Smith, starred in an editorial titled “Domestic Bliss,” and totally didn’t have an affair while Pitt was still married, Hollywood’s golden couple broke up in a very public way, and Brad moved on to become one-half of Brangelina. The Jolie-Pitts might not be a more attractive couple, but the portmanteau is certainly catchier.

CHRIS BROWN AND RIHANNA
CHRIS BROWN AND RIHANNA

It’s hard to forget what went down with Chris Brown and Rihanna. Of the argument that escalated into a physical assault, Rihanna told 20/20: “It escalated into him being violent toward me, and it was ugly….He was clearly blacked out. There was no person when I looked at him. It was almost as if he had nothing to lose. He had so much to lose. But it was almost as if he had nothing to lose. It wasn’t the same person that says I loved you. It definitely wasn’t those eyes.”

HILARY DUFF AND AARON CARTER
HILARY DUFF AND AARON CARTER

Even better than the love triangle that resulted from this Disney Channel-esque romance (looking at you, Lindsay Lohan)? The fact that Aaron Carter is still talking about it more than 10 years later.

JENNIFER LOPEZ AND BEN AFFLECK

The 6.1-carat pink diamond engagement ring. Gigli. There was a lot going on in the world of Bennifer, but, according to J.Lo, there was also a lot of love. Despite having been married before meeting Affleck, she recently revealed that the actor was “her first big heartbreak.”

LEONARDO DICAPRIO AND GISELE BÜNDCHEN
LEONARDO DICAPRIO AND GISELE BÜNDCHEN

Leonardo DiCaprio is a serial model-dater (Bar Refaeli, check. Erin Heatherton, check.), but his split with Gisele after five years of beautiful, blonde perfection was devastating to the rest of us mere mortals.

ORLANDO BLOOM AND MIRANDA KERR
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Two beautiful people, one gorgeous baby, a not-so-pretty breakup that’s resulted in some rather teenage-level petty drama.

GWYNETH PALTROW AND BRAD PITT
Gwyneth-Paltrow-Talks-About-Brad-Pitt-Ben-Affleck
So blond. So beautiful. So ’90s. The couple broke off their engagement in 1997, changed their haircuts, and crushed our dreams.

JENNIFER LOPEZ AND MARC ANTHONY
JENNIFER LOPEZ AND MARC ANTHONY

Sadly, we really thought this one was going to last, but J.Lo—and her “Booty”—isn’t wasting any time moving on. You go, girl.

ROBERT PATTINSON AND KRISTEN STEWART
ROBERT PATTINSON AND KRISTEN STEWART

Twihards everywhere will NEVER forgive K.Stew for cheating on R.Patz. However, Bella Swan and Edward Cullen will shimmer together, forever.

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