The Most Memorable Breakups in Hollywood History

Oh, Harry Styles, we have so much wonderful, hip-shaking music to thank you for. We knew you were trouble when you walked in, and even though you and Taylor might never ever, ever be getting back together, your relationship will live on in the gloriousness that is 1989.

Former co-stars Stone and Garfield seemed like the perfect couple, but the duo ended things for good in October 2015. As cute as they were together, they're still very cute as very friendly, supportive exes.

After meeting on the set of Step Up, Tatum and Dewan got married in 2009. The couple announced their divorce in April 2018, with a statement to People. "Absolutely nothing has changed about how much we love one another, but love is a beautiful adventure that is taking us on different paths for now," they wrote.

When these High School Musical stars broke up after five years together, Zac Efron—and his abs—were finally on the market. Together, they were super cute, but alone, we can just appreciate the fact that he is super, super hot.

Most people debate whether they have to give back the expensive gifts their significant others gave them because it's the right thing to do. For Anne Hathaway, after her ex-boyfriend Raffaello Follieri was convicted for swindling investors out of millions of dollars back in 2008, she had to hand jewelry she'd been given over to the FBI. When asked in an interview a few years later what her deal-breakers are when it comes to men, Hathaway jokingly replied, "Uh...fraud?" Live and learn, right?

Ah, Selena and Justin, the on-again, off-again kind of love that could only exist in a world with Instagram and Segways. Who knows what the current status of this forever tweenage couple is, but even the biggest Bieber haters feel some feelings about the ordeal, thanks to Gomez's raw, super emotional video "The Heart Wants What It Wants."

Marilyn Monroe had already been married twice—to James Dougherty and Joe DiMaggio—when she wed playwright Arthur Miller in 1956. Their marriage unraveled very publicly on the set of The Misfits—written by Miller and starring Monroe—and the two divorced before it was even released in 1961.

The naysayers were out in full force when Ashton Kutcher and Demi Moore got together. With their 16-year age difference it seemed hard to believe that it would last eight months, let alone eight years. So, when the two split in 2011, finalizing their divorce in 2013, it was a thing.

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. Still, #teamjen forever.

Shortly after Bridget Moynahan and Tom Brady split in 2006, the quarterback started dating another model: his now wife, super beautiful human Gisele Bündchen. Then—surprise—Moynahan discovered she was pregnant with Brady's son, John, and drama was born.

After 23 years, two kids, and 130 episodes of Keeping Up With the Kardashians, Bruce and Kris Jenner called it quits earlier this year. "Finally," was the reaction from everyone in America. Now Jenner can retreat to his Malibu man cave and do whatever he's doing in peace.

Fifteen years after their fairytale wedding, Princess Diana and Prince Charles divorced in a rather unfairytale fashion amid rumors of infidelity on both sides. Diana was given about $22.5 million in cash and stripped of her "Royal Highness" title, reportedly at Prince Charles' insistence.

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."

Christie Brinkley and Peter Cook's messy, mud-slinging, 2008 public divorce is the stuff tabloid dreams are made of.

Welp, you can't get much more public than a Tiger Woods-style breakup. After Tiger was revealed to be a super cheater, Elin attacked him and his car with a golf club.

They dated for 13 years, but a few years after the adorable, floppy-haired British hunk not-so-adorably cheated on Hurley with a prostitute (and was arrested for it), the two split in 2000.