25 Pop Star Breakups That Broke Our Hearts

Forget a love letter: What's a better relationship memento than the former couple's universally-panned 1986 movie 'Shanghai Surprise'? The couple divorced in 1989.

Wed in true rock star fashion—they eloped on Bonet's 20th birthday in Vegas—we wanted the rocker and "The Cosby Show" star to stay together to prove a Vegas quickie could last forever. Sadly, it didn't; they divorced in 1993.

No Doubt's breakout album 'Tragic Kingdom' relived this couple's 1994 split in oft-awkward detail. And what a cute couple they were! But, sadly, we can't have tragic heartbreakers like "Don't Speak" and a shiny-happy couple.

The Bad Boy producer and Bronx native Jenny From the Block sadly weren't meant to go down in Gangsta Love History. The couple split in 2000.

It was pop's fairy tale romance of the 2000s. All was seemingly perfect, until the Mouseketeer romance ended abruptly in March 2002.

Remember Usher's "U Remind Me" and "U Got It Bad" videos, both starring Chilli?! Sadly their collabos ended there; the couple split in 2004.

'Newlyweds' documented the young couple's almost-too-good-to-believe TV romance (who could forget the Chicken of the Sea farce?). The couple divorced in 2005, but no reality TV relationship will ever (ever!) tops theirs.

Both had red hot careers while dating, but when it cooled in April 2006, so did their success. Take a hint, guys: Rekindle and top the charts!

It was an odd couple: But, hey, when one of our favorite actors and singers unite, we don't complain. They were hot and heavy in 2002 but "mutually" called it off in February 2007.

After so many high-profile romances, it was a relief when these two celebrity serial daters finally got together. But the "sexual napalm," as Mayer described "it," wasn't meant to last; they split in early 2007.

Dupri infamously had JJ's image tattooed on his side in May 2009, which was a very sweet gesture, but ultimately a bad idea: the couple broke up later that same month. But, hey, Janet: Any man who tattoos YOUR FACE on his body is a keeper!

The pop star and the Gym Class Heroes frontman dated just as their careers were taking off. They broke up in December 2008, dated again in April 2009 and split for good a few months later. We miss the rock edge Katy had with Travie.

They collaborated on raunchy sex jams ("Blindfold Me" and "In Public") and who doesn't want more raunchy sex jams?! Sadly, they didn't; Nas and Kelis divorced in May 2010.

'Ye and Rose's "Good Life" didn't last. They split in summer 2010, and both quickly moved on, she to Wiz Khalifa and he to Kim Kardashian. Downgrades all around.

Too bad the pop-punk prince and princess didn't procreate because with Avril's clothing line that baby would've been the most stylish tot on the Warped Tour. Their divorced finalized in November 2010.

They divorced in February 2011, but now that Fall Out Boy is back together maybe there's hope for a Simpson-Wentz reunion too...?

Even Jack's ex-wife, Meg White, approved of Elson and acted as the maid of honor in their wedding! Still, they separated in June 2011... with a divorce party. How's that for ending amicably?

Sia's nickname for former girlfriend Samson (of electroclash outfit Le Tigre) was "Mr. Boop." That's reason enough to demand a reunion. That, and we're still hoping for a collabo. Sia confirmed their split on June 13, 2011 on Twitter.

The couple were a force to be reckoned with on M.I.A.'s first two albums. After splitting before her third release in 2010, '/\/\ /\ Y /\,' the record disappointed, leaving us wishing they'd get back to together... and back to making blazing tracks.

We have a feeling Mraz's 2011 break-up with his singer/songwriter fiance is what changed his tune from the lighthearted vibe of "I'm Yours" to the somber tone in "I Won't Give Up." We love both tracks, but Mr. A-Z just sounded happier then!

All hope for lasting love was lost when Sonic Youth's founding members separated after 27 years of marriage. Even worse: It means the end of their band. The October 14, 2011 split announcement led member Lee Ranaldo to confirm the band would be "ending for a while." No fair!!!

When the super producer and singer hooked up in 2009, he breathed new life into her career with a new record deal. Their divorce came two years later on October 23, 2011...and still no new album from Milian. We want that record!

It's basic rock star logic that Maroon 5 heartthrob Levine would date a Victoria's Secret Model. But it's their April 2012 split that defies logic. Adam, dude, WHAT ARE YOU THINKING?

The EDM mastermind and electro songstress sent cute, supportive tweets to each other and collaborated on banging tracks. We're not sure which we miss more: The adorable messages in our feed or the heavenly electronic tracks like "Summit" and "Bittersweet."

Pop's latest royal couple felt like the Justin and Britney for a new generation. The Biebs spills his heartache in "Nothing Like Us," proving that, yes, there really aren't any other 18-year-old stars as rich and successful as this onetime couple. Which only means one thing: They must reunite!