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Split! The Year's Biggest Breakups

Split! The Year's Biggest Breakups

From Jessica and Tony to Jon minus Kate, it was a year of dramatic endings

By Cara Lynn Shultz

Updated November 20, 2009 11:55 AM

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JESSICA & TONY

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Pals said Jessica Simpson was hoping for an engagement ring on her birthday. Instead, on the night before her 29th bash, Dallas Cowboys quarterback Tony Romo broke off his nearly two-year relationship with the singer. Sources close to the couple said her family factored into the split. "They are extremely close and when you date her, you date her family," the source said.

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JON & KATE

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He was spotted out with other women. She was accused of cheating with her bodyguard. But on the eve of the premiere of their hit TLC reality series Jon amp Kate Plus 8, Kate Gosselin filed for divorce June 23, saying he "left me no choice." In the months that followed, Jon found romance with a new girlfriend, Hailey Glassman, and the famous parents battled it out in the press, with everyone from Nancy Grace to Bethenny Frankel taking sides.

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SEAN & ROBIN

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They were on – then off. Then on – then off again. They patched things up in May, but on Aug. 13, Robin Wright Penn filed for divorce from her husband a third time. A month later, Penn was seen stepping out with Sports Illustrated model Jessica White in New York.

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RIHANNA & CHRIS

Credit: Kevin Mazur/WireImage

They were supposed to spend Feb. 8 at the Grammy Awards. But instead, Chris Brown surrendered to police for the brutal assault of then-girlfriend Rihanna. The pair briefly reconciled, but Rihanna was soon linked to Canadian rapper Aubrey "Drake" Graham, while Brown – who was sentenced to community service – told PEOPLE that he still loves his ex.

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MILEY & JUSTIN

Credit: INF

Dating an older man – 20-year-old model Justin Gaston – Miley Cyrus, 16, gushed to Glamour magazine in April that he's "the best thing that's happened to me." But only three months later she took to Twitter to share feelings about their split. "Tears are words the heart can't express," Cyrus Tweeted. Still, in less than a week, she had reconnected with ex Nick Jonas.

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CHRIS & GREG

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Just 15 months after marrying, tennis star Chris Evert and golfer Greg Norman separated in early October. The reason? Friends of the couple – who left longtime spouses for each other – say interacting with each other's children caused problems in the marriage. The couple's reps told PEOPLE, "Chris and Greg will remain friends and supportive of one another's family."

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AVRIL & DERYCK

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On Oct. 14, Avril Lavigne made it final, seeking a divorce from her fellow Canadian pop-punker, Deryck Whibley of Sum 41, after three years of marriage. What went wrong? Sources said Avril – and in the weeks that followed the split, she was spotted out with Wilmer Valderrama.

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JIMMY & SARAH

Credit: Michael Desmond/ABC

After giving their romance another shot – the couple had split last year but reunited a few months later – Jimmy Kimmel and Sarah Silverman officially ended their relationship in March. Kimmel kept his sense of humor, appearing on The View dressed as Rosie O'Donnell and saying of the breakup, "What do you think happened? I'm a 41-year-old man with a bra filled with Koosh balls."

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JULIANNE & CHUCK

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"We spend a lot of time apart from each other – so we're just taking a little break right now," Julianne Hough told PEOPLE about the reason behind her November split from beau Chuck Wicks. Still, the country cuties attended the CMA Awards together.

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BILLY & KATIE LEE

Credit: William Regan/Globe

The Piano Man and his wife of five years, former Top Chef host Katie Lee Joel, announced their split on June 17 after five years of marriage. "Billy amp Katie remain caring friends with admiration and respect for each other," their reps said in a joint statement.

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LINDSAY & SAMANTHA

Credit: Seth Browarnik/Red Eye Productions

The twosome started the year denying rumors of a split, with Lindsay Lohan taking to her MySpace blog to defend her relationship with Ronson, proclaiming, "We did NOT break up!" After a tumultuous on-and-off again relationship – Lohan's was cited as the cause of their troubles – the pair were officially "off" by mid-summer. Or were they? It wasn't long before they were seen (again) hanging out in L.A.

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CARRIE & ARTEM

Credit: Vince Flores/Celebrity Photo

Time for a new tango partner: Dancing with the Stars judge Carrie Ann Inaba announced her split with fellow dancer Artem Chigvintsev in February. It was one of the more civil breakups of the year, with Inaba praising her ex for being "a fine gentleman."

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USHER & TAMEKA

Credit: Getty

Married two years – during which they welcomed two children – Usher filed for divorce from wife Tameka Foster on June 12. The singer turned his pain into inspiration, however, penning a song called "Papers." "I done turned into the man I never thought I'd be/I'm ready to sign them papers," he sings on the track.

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AMY & BLAKE

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The tumultuous two-year marriage of Amy Winehouse and Blake Fielder-Civil came to an unceremonious end on July 16, when the couple was in London. The reason? Fielder-Civil charged that Winehouse was unfaithful – and although Winehouse had said she wouldn't, the singer didn't contest it in court, admitting to adultery.

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JANE & BRADLEY

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In one of the year's more shocking splits, Jane Kaczmarek and Bradley Whitford filed for divorce in Los Angeles on June 19. The couple, who have three children together, had been married for nearly 16 years.

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KIM & DAVID

Credit: Fame

The American Idol alums – David Cook won season seven, Kimberly Caldwell competed in season two – announced their split in January, but maintain that the breakup was amicable.

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COREY & SUSIE

Credit: Scott Kirkland/INF

Anyone who watched The Two Coreys saw how in love Corey Feldman and Susie Sprague were. Yet Sprague filed for divorce on Oct. 22 – shocking her husband of seven years. Feldman issued a statement after the split, saying he "has done nothing to contribute to the demise of the marriage."

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EMMY & JUSTIN

Credit: INF

He was the husband no one knew she had, but this September, music exec Justin Siegel filed for divorce after a year-and-a-half marriage to actress Emmy Rossum. Siegel cited irreconcilable differences – and his ex was soon linked to Counting Crows frontman Adam Duritz.

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MEL & ROBYN

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They spent nearly 30 years together. But on April 13, Robyn Moore sought a divorce from husband Mel Gibson. Since the couple have no prenup, the split could be the costliest in Hollywood history. The actor, who maintains that he and his wife split three years before the formal filing, is expecting a child with his Russian musician girlfriend, Oksana Grigorieva.

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SHANNA & TRAVIS

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Although estranged twosome Shanna Moakler and Travis Barker reunited after his 2008 plane crash, their dramatic on-and-off romance was decidedly off again in April, when Moakler took to her blog to refute rumors of an affair. The online digs continued on Twitter when Barker called the former beauty queen a "deadbeat mom." The two eventually managed to shelve the drama, with Moakler telling PEOPLE, "We have a real love for one another, and we always have."

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DEMI & TRACE

Credit: Sthanlee B. Mirador/Shooting Star; Joe Kohen/WireImage

Disney darling Demi Lovato and Metro Station frontman (and Miley's brother) Trace Cyrus announced their split on July 21. "I'm always on the other side of the world and so is she, so it just seemed like something that can't work out at this time," Cyrus told PEOPLE.

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BRISTOL & LEVI

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They had planned on getting married after completing high school, but in early March, the daughter of former Alaska Gov. Sarah Palin and Levi Johnston broke up, just two months after she gave birth to son Tripp. Johnston spent the year enjoying his newfound fame, dishing on the Palin household to Vanity Fair and inking a deal to pose nude in Playgirl.

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JENNIFER & ROSS

Credit: Gilbert Flore/Celebrity Photo

Three months after news broke that Ghost Whisperer star Jennifer Love Hewitt had split from Scottish actor Ross McCall, costar Jamie Kennedy declared his love for her on Ryan Seacrest's radio show. The two were soon inseparable, with Hewitt even nursing Kennedy back to health after a hospitalization for kidney stones.

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MAKS & KARINA

Credit: Paul Hiffmeyer/Disneyland

They were flawless partners on and off the dance floor. But Dancing with the Stars pros Karina Smirnoff and Maksim Chmerkovskiyshocked friends with news that they were breaking off their engagement this September. Although Maks said they reunited to perform during the Emmys because "I knew how big of a deal it was for her," he changed his amiable tune a few weeks later, telling PEOPLE, "I feel completely betrayed. I'm done."

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JOE & CAMILLA

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After reports spread that Camilla Belle and Robert Pattinson were an item, the actress and Jonas Brother announced their split on July 27 – taking care to again deny the rumors. "There is no third party involved and they care deeply about each other and will remain friends," the twosome said through a rep.

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NAS & KELIS

Credit: Michael Williams/Startraks

"Milkshake" singer Kelis was seven months pregnant with Nas's son when she filed for divorce from the rapper in April. Although Nas said the singer didn't deserve alimony, a day after Kelis gave birth he was ordered to pay $40,000 a month in child support.

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MILO & HAYDEN

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The 12-year age difference proved too much for Hayden Panettiere and her Heroes costar Milo Ventimiglia this year, as the couple split in February, ending their romance of more than a year.

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KELLY & DANIEL

Credit: Michael Williams/Startraks

Gossip Girl star Kelly Rutherford's divorce from husband Daniel Giersch has proved to be just as drama-filled as one of the storylines on her hit show. She says she had to call the police on her husband, while he claimed he was never notified about their daughter Helen's birth in June. Rutherford eventually won a restraining order against her husband, admitting that she's going through a "challenging time."

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LEANN & DEAN

Credit: Denise Truscello/WireImage

Following rumors that LeAnn Rimes had cheated on her husband of more than seven years, Dean Sheremet, with married Northern Lights costar Eddie Cibrian, news broke that Rimes and Sheremet were officially separated. Cibrian and the country singer filed for divorce within days of one another – and the costars soon took their romance public.

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JAMES & HEATHER

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After nearly six years together, Dawson's Creek alum James Van Der Beek filed for divorce from his wife, actress Heather McComb, in late November. The couple had announced they were separating in June, but according to his rep, "They remain good friends."

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By Cara Lynn Shultz

Account

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Split! The Year's Biggest Breakups

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JESSICA & TONY

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JON & KATE

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SEAN & ROBIN

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RIHANNA & CHRIS

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MILEY & JUSTIN

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CHRIS & GREG

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AVRIL & DERYCK

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JIMMY & SARAH

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JULIANNE & CHUCK

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BILLY & KATIE LEE

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LINDSAY & SAMANTHA

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CARRIE & ARTEM

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USHER & TAMEKA

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AMY & BLAKE

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JANE & BRADLEY

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KIM & DAVID

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COREY & SUSIE

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EMMY & JUSTIN

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MEL & ROBYN

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SHANNA & TRAVIS

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DEMI & TRACE

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BRISTOL & LEVI

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JENNIFER & ROSS

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MAKS & KARINA

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JOE & CAMILLA

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NAS & KELIS