Worst Celebrity Breakups
We're still crying over these Hollywood split ups!
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Celebrity Love Gone Wrong

rihanna, chris brown, celebrity breakups rihanna and chris brown at the 2009 pre grammy party We love our Hollywood couples. When their hearts break, ours go with it! Check out our list of most heartbreaking celeb breakups to date.

Demi Lovato and Trace Cyrus

demi lovato, trace cyrus, celebrity breakups demi lovato and trace cyrus #20-Demi Lovato and Trace Cyrus: We don\'t know which surprised us more, the fact that these two started dating to begin with or that the Metro Station singer dated little sis Miley\'s toughest competition for the teen princess throne!

Camilla Belle and Joe Jonas

camilla belle, joe jonas, celebrity breakups camilla belle and joe jonas #19-Camilla Belle and Joe Jonas: We weren\'t particularly attached to these two, but apparently Joe was! He changed the lyrics to one of his songs at a concert to \"Get a rep for breakin\' hearts, now I\'m done with superstars\" to \"Get a rep for breakin\' hearts, now I\'m done with movie stars.\" Zing!

Madonna and Guy Ritchie

madonna, guy ritchie, madonna divorce, celebrity breakups madonna and guy ritchie #18-Madonna and Guy Ritchie: The rumor mill was buzzing when Madonna was having Yankee star Alex Rodriguez over to her Manhattan apartment. His wife Cynthia filed for divorce in July 2008 and Madonna and Guy followed in October. Coincidence?

Amy Winehouse and Blake Fielder-Civil

amy winehouse, blake fielder-civil, celebrity breakups amy winehouse and blake fielder civil walking down the street #17-Amy Winehouse and Blake Fielder-Civil: These were two hot messes together. Between Civil\'s jail time and Wino\'s crazy outbursts we thought they were a match made in dysfunctional heaven. Alas, they divorced in July 2009.

Selena Gomez and Nick Jonas

selena gomez, nick jonas, celebrity breakups picture of selena gomez and nick jonas #16-Selena Gomez and Nick Jonas: These two were just as cute as apple pie! They kept their lips zipped on their relationship, but were rumored to break it off right before Valentine\'s Day in 2008. Aww...

Rachel McAdams and Ryan Gosling

rachel mcadams, ryan gosling, the notebook, celebrity breakups rachel mcadams and ryan gosling on the red carpet at the 13th annual screen actors guild awards in 2007 #15-Rachel McAdams and Ryan Gosling: Any couple that meets on the set of The Notebook would be perfect together. After breaking our hearts with the film, they broke our hearts in real life when splitting in 2007. Fans even yelled at Ryan on the street for letting Rachel go!

Pink and Carey Hart

pink, carey heart, celebrity breakups pink and carey hart at the t mobile sidekick lx launch party in la 2009 #14-Pink and Carey Hart: We\'re not sure if these two even belong on this list. They divorced in February 2008 but by May 2009 were back together! Hopefully this time sticks.

Jennifer Aniston and John Mayer

jennifer aniston, john mayer, celebrity breakups jennifer aniston and john mayer at the 2009 vanity fair oscar party #13-Jennifer Aniston and John Mayer: Our hearts bled for poor Jen, who was single again this year after an on-again, off-again relationship with swooner John Mayer. The last time they broke up was allegedly over John\'s obsession with Twitter!

Kate Hudson and Chris Robinson

kate hudson, chris robinson, celebrity breakups kate hudson and chris robinson at the four feathers premiere in 2002 #12-Kate Hudson and Chris Robinson: We loved these two because of their odd couple factor. Kate as the boho glam actress and Chris as the Black Crowe rock star. Kate started filming You, Me and Dupree in 2006 and the two split shortly after. Since then she\'s been linked to Owen Wilson and recently Alex Rodriguez. That Yankee gets around the Hollywood scene!

Reese Witherspoon and Ryan Phillippe

reese witherspoon, ryan phillippe, celebrity breakups reese witherspoon and ryan phillippe at the premiere of legally blonde 2 in 2003 #11-Reese Witherspoon and Ryan Phillippe: 2006 was a bad year for Hollywood relationships! This power couple split after seven years of marriage and two kids! Phillippe was rumored to start dating his now girlfriend Abbie Cornish while still married, though both admitted to reporters that they went to couples therapy.

Jessica Simpson and Tony Romo

jessica simpson, tony romo, celebrity breakups jessica simpson and tony romo at the 16th annual country thunderusa in 2008 #10-Jessica Simpson and Tony Romo: You know a relationship is off to a rough start when an entire NFL team blames you for being a bad luck charm! Still, these two gave it a second shot only to break up again in July 2009.

Miley Cyrus and Justin Gaston

miley cyrus, justin gaston, celebrity breakups miley cyrus and justin gaston spotted out in los angeles in 2009 #9-Miley Cyrus and Justin Gaston: Miley caught some heat for dating this 20-year-old model. When they broke up in June 2009 they both took to Twitter to grieve. \"Tears are words the heart can\'t express,\" Cyrus tweeted. Gaston counter-tweeted, \"How many tears are in there? They\'ve gotta run out soon, right?\"\r\nOh the drama!

Taylor Swift and Joe Jonas

taylor swift, joe jonas, celebrity breakups taylor swift and joe jonas at the 2008 mtv video music awards #8-Taylor Swift and Joe Jonas: It was just a year ago when these two were sitting together at the MTV Video Music Awards. Joe dumped Taylor over the phone, which she did not take too kindly. She wrote about him on her Forever and Always album and poked fun at the Jonas Brother dolls on her MySpace page. \"See, this one even comes with a phone. So he can break up with other dolls.\" Oops!

Kim Kardashian and Reggie Bush

kim kardashian, reggie bush, celebrity breakups kim kardashian and reggie bush at the russell simmons rush philanthropic arts event in 2009 #7-Kim Kardashian and Reggie Bush: We were so happy when Kim was getting serious with this pro football player, but due to their busy schedules they called it quits. Weeks after they were spotted out together in New Orleans smiling and flirting. Sometimes you can\'t stop true love!

Kate and Jon Gosselin

kate gosselin, jon gosselin, celebrity breakups kate and jon gosselin at the discovery upfront at jazz at lincoln center in 2009 #6-Kate and Jon Gosselin: Mostly, we feel bad for the plus 8 in the Jon and Kate Plus 8 clan. We also feel bad for us, as they are always in the tabloids now. Between Jon\'s midlife crisis and Kate\'s constant interviews, we liked these two together better for the sheer fact that they weren\'t in the limelight all of the time!

Lindsay Lohan and Samantha Ronson

lindsay lohan, samantha ronson, celebrity breakups lindsay lohan and samantha ronson at the charlotte ronson afterparty in new york 2009 #5-Lindsay Lohan and Samantha Ronson: We have to admit, Lindsay seemed a little more balanced while dating Sam. They seem to still be in contact (especially via Twitter!), but since their split, shes been spotted showing up at her house in the middle of the night banging on the door all because Sam was out with another friend! Oh Lindsay...

Jennifer Aniston and Brad Pitt

jennifer aniston, brad pitt, celebrity breakups jennifer aniston and brad pitt at the vanity fair oscar party in 2000 #4-Jennifer Aniston and Brad Pitt: We don\'t care how long ago it was, these two were the Hollywood couple before splitting in 2005. Sure, Brad and Angie seem to be going strong with their army of kids but sometimes we miss the good old days of Brad and Jen.

Jessica Simpson and Nick Lachey

jessica simpson, nick lachey, celebrity breakups jessica simpson and nick lachey at the 2003 mtv video music awards #3-Jessica Simpson and Nick Lachey: Were all those countless hours we dedicated to watching marathons of Newlyweds wasted? We thought for sure there might be a reunion with these two since they both recently became single in the same month, but both say that ship has sailed.

Rihanna and Chris Brown

rihanna, chris brown, celebrity breakups rihanna and chris brown at clive owens pre grammy party in 2008 #2-Rihanna and Chris Brown: The world was shocked after Chris was charged with two felonies when he assaulted Rihanna after a pre-Grammy party in 2009. They\'ve been spotted together a few times since, though now that the case is closed he isn\'t allowed to have any contact with Rihanna for five years.

Britney Spears and Justin Timberlake

britney spears, justin timberlake, celebrity breakups britney spears and justin timberlake at the 29th annual american music awards #1-Britney Spears and Justin Timberlake: Laugh all you want, these two were a pop powerhouse couple! Since the split, Justin seems to have more luck in the love department than poor Brit but we think deep down, they miss each other as much as we miss them as a couple!
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