Look Back at the Worst Celebrity Breakups

Britney Spears and Kevin Federline
Was anyone surprised at this one-way ticket to Splitsville? While to 99.9% of people this split was a forgone conclusion, it continued to grow in awfulness seemingly by the minute. Accusations of Britney's inability to be a proper mother to her children, heavy partying, and subsequent craziness (read: shaving her head on impulse), pushed the needle of support toward (gasp!) K-Fed. But then he started his own breakup pot-stirring tomfoolery by using the legal system to further his own get-rich-quick-via Britney schemes. Luckily, the two have moved on...as most mid-to-late twenty-ish parents do.. Britney is now in the midst of a career revitalization and Federline is working on curbing that healthy appetite.

Heather Mills and Sir Paul McCartney
This is not only one of the worst breakups in celebrity history, but it's notable because Heather Mills singlehandedly made almost everyone in the world realize they could actually not have compassion on someone with a prosthetic leg if said person was diabolical. Paul was coming off losing his wife of many years, who was loved and adored by fans around the globe, and Dr. Roger Rhoades -- a relationship counselor who has appeared on shows like "Oprah", "Rickie Lake", and "Jenny Jones" -- thinks this might have contributed to the breakup. "A man who has had a good long marriage will try to repeat it, but will never be able to do so...and the new woman will resent him for it," says the good doctor. Things started to go sour when the future "Dancing With the Stars" contestant began making comments in public about how boring Sir Paul was and how he had no friends. When they finally split, she asked for nearly $210 million while representing herself in court. When she started tossing around accusations and claims against the beloved Beattle, her case started falling apart -- partly because her first husband testified against her and her own book, Life Balance: The Essential Keys to a Lifetime of Wellbeing, contradicted her claims. For his part, McCartney tried to keep quiet and classy throughout, even when his soon-to-be ex dumped a jug of water on his attorney's head near the end of the trial.

Nicole Kidman and Tom Cruise
This out-of-nowhere severing of ties was even more perplexing because of Nicole's believable bewilderment and Tom's statement regarding the divorce: "Nicole knows why." Because Tom's PR was rock solid back then (pre-couch jumping/pre-Matt Lauer debating), he declined interviews and dodged questions on the subject, while Nicole was still asking questions about what went wrong and admitting she begged Tom to try marriage counseling. Dr. Rhoades believes stardom killed their relationship, "When you have two bright and shining stars close together, they cannot help but burn up the relationship trying to stay bright." Astrological metaphors aside, what else was the world to do but wonder...was it a butting of heads over religion? Did one of them cheat? Was Tom tired of being five inches shorter than Nicole? We may never know the real reason, but this breakup sold a lot of magazines and is still being talked about all these years later.

Brad Pitt and Jennifer Aniston
For their credit, these two have mostly taken the high road on this. Understandably for Brad, he hasn't said zilch about their split since much of the blame has been heaped on him by the media. As the story goes, Brad and Angelina Jolie -- known jointly to you as Brangelina -- met on the set of Mr. & Mrs. Smith and the rest is history. The few trickles of reports from the crew on the set did mention how hot the sparks were between the two mega-stars, but we weren't there to confirm. Aniston has since opened up a bit about the breakup by declaring that Angelina's describing how she fell head-over-high heels for Brad on the set "was very uncool." This one ranks as one of the worst because it broke the hearts of all the romantics out there that still want to believe two unbelievably attractive and talented people can be together forever. Guess here's hoping the unbelievably attractive and talented Brad and Angelina can go the distance.

Alex and Cynthia Rodriguez
When Cynthia Rodriguez filed for divorce from her All-Star husband of six years, she claimed it was because of his "long period of infidelity." The last straw apparently was A-Rod spending an evening behind closed doors with Madonna. A night Cynthia's lawyer said was "an affair of the heart" and not of a sexual nature. Dr. Rhoades thinks there's definitely something to that celebrity meeting. "When a man is at a certain level, he sees himself with people from the level he is currently at," he says. "But if the level in his mind is greater, then the people on the other [lower] level won't do, and to him, don't fit." A-Rod was in the process of filing his own divorce papers because he alleged Cynthia refused to try and repair their failing marriage. Maybe they couldn't coordinate her shopping schedule with his dating schedule. But that's just us. Any bets on if Cynthia got the centaur picture in the settlement?

Levi Johnston and the Palin Family
For all the jabs Sarah Palin has taken in the press because of her politics, moose hunting, or statements about seeing Russia from her pad, it all now takes a back seat to her daughter's baby daddy and his mega-rift with the entire family. First, aspiring actor Levi Johnston gets Bristol Palin preggers during an election year that has her mother front and center. Then after the teenagers break up, he decides to cash in and make something of himself...in Playgirl magazine. He also started taking interviews with the likes of "The Early Show" and spilling secrets about the Palins. Whether the secrets are true or not, this one kept getting uglier. And still is. Bristol Palin's mom hasn't exactly taken the high road when she recently quipped about Levi's new career "in porn" while on "Oprah". She did state that Bristol's ex-prom date would be welcome at the Palin Thanksgiving table -- at which Levi scoffed and quickly dismissed. This one is bound to continue grabbing headlines -- especially since two of its players are in the business of promoting themselves these days. We have to wonder what Bristol actually has to say about all this?

Hulk and Linda Hogan
This one is just icky. Maybe it's the fact that Hulk Hogan nabbed himself a girlfriend that looks exactly like his daughter immediately after the split. Or maybe It's because Linda nabbed herself a 19-year-old boyfriend who certainly could pass as the son of one of the Nelsons (we've been waiting years to work in a Nelson reference somewhere). Or perhaps it's because both of them brought their new significant others to the divorce proceedings. Seriously. When Linda filed for divorce from the Hulk, things really started going south of amicable. There was Linda's accusations against her ex that he was stalking her and then the story of her rumored prescription drug habit funded by her alimony came above ground. "Some people who work well on the way up, will not work on the way down," says Dr. Rhoades. Whether the demise of the Hogan's was due to Hulk's fading star or not, this one was about as ugly as Hulk's recent bloody mess after a 'tussle' with Ric Flair.

The Gosselins
This is the grandaddy of splits. The Gosselins became celebs for having a whole mess of kids and allowing themselves and their children to be filmed shortly thereafter. But as gossip mags are wont to do, reports started surfacing about the behind-the-scenes bickering. From Jon's partying ways and lazy ways, to Kate's bossiness and tantrums, the rumors kept swirling. Appears now, some of them were true. When the split was announced on their show, the floodgates of ugly opened wide. Jon got a bachelor pad in NYC and hit the town with a bevy of beauties and plenty of adult beverages. Meanwhile, Kate hit the interview circuit and didn't hold back her thoughts for her estranged hubby. Then Jon gave counter-interviews. Then the cops get called during a heated argument at the house. And then there's that ugly lawsuit with TLC. This is the Energizer Bunny of breakups. And it's still going...

Filed under:
• Famous Couples
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• Celebrity Fights
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• Splitsville
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• Troublemakers
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• Celebrity Scandal
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• Brad Pitt
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• Demi Moore