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20. Sean and Robin are at the bottom of the list, because they've done this before. The actors, who got together in 1989 and have two kids, have filed for divorce twice before, only to reconcile and call the split off. That they are going through with it this time is what is kind of shocking. Click through to review even more shocking splits ... and see who we picked as the year's biggest breakup surprise. (AP)![James Van Der Beek and Heather McComb]()
19. The ‘Dawson’s Creek’ star married actress Heather McComb in 2006. Their separation was announced in June, and Van Der Beek filed for divorce in November. We can't believe that Dawson didn't live happily ever after. For more pics of James Van Der Beek, visit x17online.com![Jane_Kaczmarek_and_Bradley_Whitford]()
18. The couple, who had been married for nearly 16 years, filed for divorce in June. The actors have three children together. They seemed so happy! (AP)![Hayden Panettiere and Milo Ventimiglia]()
17. The couple split in February, ending their romance of more than a year. Maybe it was the 12-year age difference; the ‘Heroes’ costars started dating when he was 30 and she was just 18. Yikes. For more pics of Hayden Panettiere, visit x17online.com![Nas_and_Kelis]()
16. "Milkshake" singer Kelis filed for divorce from the rapper in April when she was seven months pregnant with his son. Kind of harsh. (AP)![Katy Perry and Travis McCoy]()
15. Perry dated Gym Class Heroes frontman Travis McCoy on and off for several years but broke up this spring. The provocative pop star began dating UK comedian Russell Brand in September. Cute girls always go for the funny guys. For more pics of Katy Perry, visit x17online.com![Emmy Rossum and Jason Siegel]()
14. It was revealed that the 23 year-old starlet had a year-and-a-half-long secret marriage when music exec Jason Siegel filed for divorce from her this year. Rossum is currently dating Counting Crows frontman Adam Duritz, 45. What is his special charm? For more pics of Emmy Rossum, visit x17online.com![Jimmy_Kimmel_and_Sarah_Silverman]()
13. We were bummed with this funny couple called it quits this year. The on-again, off-again romance officially ended in March. That's what you get for sleeping with Matt Damon and Ben Affleck. (AP)![Miley Cyrus and Justin Gaston]()
12. 16 year-old Miley took to Twitter to share about her split from 20 year-old underwear model Justin Gaston. "Tears are words the heart can't express," she Tweeted. For more pics of Miley Cyrus, visit x17online.com![Billy_Joel_and_Katie_Lee_Joel]()
11. Another age-difference disaster! The Piano Man and his wife of five years, former ‘Top Chef‘ host Katie Lee Joel, announced their split in June. Billy, 60, and Katie, 27, had been married for five years. We thought they'd go at least eight. (AP)![Justin_Timberlake_and_Jessica_Biel]()
10. Reports have been swirling for months that Hollywood’s hottest young romance is over, though it has yet to be confirmed by the SexyBack singer himself. But we never see these kids out together like they used to be anymore, so something's going on. (REUTERS)![Usher_and_Tameka_Raymond]()
9. After two years of marriage and two sons, the much-maligned relationship is over. The entertainer filed for divorce in June. (AP)![Bristol_Palin_and_Levi_Johnston]()
8. These Alaska teens caused quite the stir when it was revealed that then 17 year-old Bristol, the daughter of former vice-presidential candidate Sarah Palin, was pregnant. It was announced that the two would be married, but they broke up this spring, just months after Bristol gave birth. The drama continued when Levi exposed himself in ‘Playgirl’ magazine. Looks like Bristol made the right move. (AP)![Avril Lavigne and Deryk Whibley]()
7. It was a match made in Hot Topic, but the pop punk couple announced their split in September. Lavigne, who married the Sum 41 frontman at the tender age of 21, filed for divorce in October. For more pics of Avril Lavigne, visit x17online.com![Rosie O'Donnell and Kelli Carpenter]()
6. Rosie recently admitted that she and Kelli, her wife of five years, had split some time ago, which was strange. The couple has four children together. (AP)![Jessica_Simpson_and_Tony_Romo_first]()
5. It was reported in July that the singer and her football pro beau were no more. The Cowboys quarterback was reported to have sacked "Yoko Romo" the night before her 29th birthday. What a guy. (AP)![Mel_Gibson_and_Robyn_Moore]()
4. The Catholic star shocked the public when he left the mother of his seven children for a young Russian pop star. After 29 years of marriage, wife Robyn filed for divorce in April. In October, Gibson’s girlfriend, Oksana Grigorieva, gave birth to their daughter. Now it all makes sense... For more pics of Mel Gibson, visit x17online.com![Rihanna_and_Chris_Brown]()
3. They were pop music’s golden couple until February, when reports surfaced that Brown had beat his girlfriend during a fight in a car right before the Grammy Awards show. A gruesome police photo of Rihanna’s battered and bruised face was leaked, shocking fans. After a brief reconciliation, they broke up for good. (REUTERS)![LeAnn_Rimes_and_Dean_Sheremet]()
2. Country star Rimes shed her wholesome image this July when she left her dancer husband for married actor Eddie Cibrian. ‘Us Weekly’ said LeAnn was having an affair her Lifetime special co-star Cibrian, citing restaurant security tapes that showed them kissing. Eddie and LeAnn have since left their respective marriages and are still together. Eddie has even since sued 'Life & Style' magazine for saying he was subsequently cheating on LeAnn! Now that's love. (AP)![Jon_and_Kate_Gosselin]()
1. The 'Jon and Kate Plus Eight' reality superstars, whose whole life was based on them being together and raising all of those kids on TV, shocked everyone, and ensured months of tabloid covers, when they split amidst allegations of cheating. The reality stars then announced on a June episode that they were separating, and have since divorced. The popular show, which featured Jon and Kate raising their eight children, saw its ratings skyrocket during the scandal, but was then was canceled as Jon alleged that the children were not faring well having their every waking minute videotaped. TLC, the network that aired the show, and was the Gosselins' employer, is now suing Jon. All of America is still traumatized at having witnessed the public disintegration of a once-beloved reality show family. It was like if the Cunningham family broke up on 'Happy Days' and you had to see Richie and Joanie bawling their eyes out every week. The Gosselins definitely could have benefited from advice from The Fonz. (AP)The 20 Most Shocking Splits of 2009
While we wait out the Tiger drama, FOX411 ranks the biggest Hollywood breakups of the year...
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- The 20 Most Shocking Splits of 2009
