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.
Michael Ochs Archives
Gwen Stefani + Tony Kanal
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.
Miley Cyrus + Liam Hemsworth
Miley Cyrus met Liam Hemsworth in 2009 while filming the big screen version of Nicholas Sparks' 'The Last Song.' Although the movie bombed, their love blossomed. Three years later, Cyrus got engaged to the 'Hunger Games' hottie—but less than two years later, they called it quits. In a post-split interview, Miley told Ellen DeGeneres that 'Bangerz' tells the story of their love, from its blissful start to its sputtering stop.
Jennifer Lopez + Diddy
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.
Justin Timberlake + Britney Spears
It was pop's fairy tale romance of the 2000s. All was seemingly perfect, until the Mouseketeer romance ended abruptly in March 2002.
Justin Bieber + Selena Gomez
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 teen stars as rich and successful as this onetime couple. Which only means one thing: They must reunite!
Usher + Chilli
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.
Taylor Swift + Harry Styles
Most guys Taylor Swift dates get a song written about them and that's it. But the One Direction lad got a song ("I Knew You Were Trouble") plus a catty shoutout at the GRAMMYs where Swiftie mocked his accent. While the pair will never ever (ever ever) get back together, we do think they were a cute couple.
Jessica Simpson + Nick Lachey
'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.
Ciara + Bow Wow
Both had red hot careers while dating, but when it cooled in April 2006, so did their success. But Ciara staged a serious comeback in 2013... coincidentally, the same year she started dating her now-fiance Future.
Alanis Morissette + Ryan Reynolds
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.
Janet Jackson + Jermaine Dupri
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!
Katy Perry + Travie McCoy
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.
Ben Gibbard + Zooey Deschanel
The couple made in hipster heaven. We always imagined the 'New Girl' actress skipping around a meadow of flowers while her Death Cab for Cutie hubby crooned out poetic love tunes. But after two years of marriage, the singer/actress filed for divorce in late 2011. Seriously, what could have possibly gone wrong?
John Mayer + Jessica Simpson
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.
Lenny Kravitz + Lisa Bonet
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.
Nas + Kelis
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.
Kanye West + Amber Rose
'Ye and Rose's "Good Life" didn't last. They split in summer 2010, and both quickly moved on, she to now-husband Wiz Khalifa and he to soon-to-be-wife Kim Kardashian. Downgrades all around.
Pascal Le Segretain
Avril Lavigne + Deryck Whibley
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.
Ashlee Simpson + Pete Wentz
They divorced in February 2011, but now that Fall Out Boy is back together maybe there's hope for a Simpson-Wentz reunion too...?
Ellie Goulding + Skrillex
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."
Jack White + Karen Elson
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, and after two years of messy legal wrangling, they officially divorced in 2013.
Sia + JD Samson
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.
M.I.A. + Diplo
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.
Jason Mraz + Tristan Prettyman
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!
Adam Levine + Anne Vyalitsyna
Some people might have yelled, "Dude, what are you thinking?!?" when news broke that the Maroon 5 heartthrob and the Victoria's Secret Model broke up. Levine has actually snagged himself another VS model—Behati Prinsloo—are currently engaged, but they haven't had adorable onstage interactions like Adam and Anne did in the past.
Thurston Moore + Kim Gordon
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!!!
The-Dream + Christina Milian
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!
Hilary Duff + Mike Comrie
Years after her 'Lizzie McGuire' days, we were happy to see 23-year-old good girl Hilary Duff find young love with Canadian hockey player Mike Comrie. Yet after three years of marriage, the two announced a split. Can't the good girl just win for once?!?