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Jen, Brangelina, and the Ten Worst Celebrity Breakups

The December 2008 Vogue — featuring a crabby-looking Jennifer Aniston and a cover blurb trumpeting yet another wronged-woman comment about Angelina (“What she did was very uncool”) — could easily have come out in 2007. Or 2005, for that matter: Three years and nine months after Brad Pitt and Aniston separated, we’re hearing stale scoop as if it happened yesterday. Fueled anew by Vogue’s out-of-context cover line, the split’s increasingly ugly tabloid life may eventually exceed that of the marriage itself. And it’s in good company: In honor of The Feud That Won’t Die, here’s our highly scientific (read: based on our memories) list of the top ten other worst Hollywood breakups in recent memory.

1. Heather Mills and Paul McCartney: With most of the British press calling her a money-grubbing tart, Mills fired back by alleging Paul was an abusive and boring drunk who hid her prosthetic leg and forced her to crawl to the loo. They spewed vitriol for almost two years until the settlement was finalized, at which point Mills pocketed $38.5 million and punctuated it by chucking water in Macca’s lawyer’s face. Melrose Place would’ve loved her.

2. Anne Hathaway and Raffaello Follieri: Anne Hathaway herself called her bust-up with the now-jailed Follieri earth-scorchingly bad. We can’t disagree: Anything that ends with your pathological-liar boyfriend under investigation by the FBI for cheating church officials and others out of large sums of money and requires you to surrender all your jewelry to the authorities is tough to beat. Unless you are Heather Mills.

3. Charlie Sheen and Denise Richards: Their tacky, gross behavior took divorce to new, fascinating levels of tacky gross-itude. Two years of rapid-fire mud-slinging — she claimed he threatened to kill her and ogled underage naked boys online; he painstakingly issued repeated passive-aggressive denials — ensured that the biggest losers are their kids, who have countless tabloid souvenirs of how much their parents hate each other.

4. Ben Affleck and Jennifer Lopez: Remember the heyday of Bennifer 1.0, when a faux-tanned Ben made bum-massaging cameos in J.Lo’s videos? And she went on Dateline to gush about how she loves to make Ben Shake and Bake chicken? And then the Enquirer claimed Affleck cheated with a bunch of Canadian strippers, the wedding was “postponed” at the last minute, and next thing you know, they were kaput? That was fun. Although probably not for them.

5. Madonna and Guy Ritchie: Rumor has it Madge cheated on Guy with A-Rod, but rumor also has it that Guy is a total jerk. We’ve also heard there isn’t a prenup, so this fresh but festering one could get spectacularly nasty. Time will tell, but we wouldn’t want to fight Madonna on anything, especially since she’s hired Paul McCartney’s divorce lawyer. Also, we’ve seen her biceps.

6. Tom Brady and Bridget Moynahan: Kids, don’t have ex sex, or else you might end up skulking around Los Angeles looking (understandably) sour-faced and hugely pregnant while your hot quarterback baby daddy shacks up with a Victoria’s Secret model. The tabloids branded him a hopeless cad; she allegedly refused to speak to him at the birth. On one hand, we feel you, sister. On the other, isn’t it dirty pool to use your baby to make a point?

7. David Duchovny and Tea Leoni: It’s a tale as old as time: Husband allegedly sleeps with his tennis instructor; husband claims to be a sex addict and goes to rehab; he and wife ultimately divorce … in part because she’s allegedly been hooking up with Billy Bob Thornton. Bonus points for the surprise ending there.

8. Tom Cruise and Nicole Kidman: He allegedly, and so very gently, called their ten-year marriage a “passionless hell” and then explained its demise thusly: “Nicole knows why.” Apparently, his chatty, couch-jumping side was on vacation. The more Nicole waxed confused, the less Tom said, leaving the grapevine to seek answers everywhere from possible infidelity to Scientology to her sad rumored miscarriage — all of which got dredged up again once he hopped on the marriage-go-round with sudden love goddess and fertile-myrtle Katie Holmes. It’s dizzying, and we’re tired.

9. Sophia Bush and Chad Michael Murray: This didn’t get as much press as the others, but think how awkward it would be if your husband allegedly cheated on you with Paris Hilton, you had to annul the marriage less than six months into it, and then you still had to go to work with him every day and occasionally make out with him. This is why they advise against dating co-workers.

10. Balthazar and Rosetta Getty: When your husband is snapped frolicking with a topless Sienna Miller in a twee little sailor hat, there is no more Mrs. Nice Mother-of-Four. Rosetta stayed above the fray, but the war of words — and smug photos of the couple “in love” — turned ugly when Miller’s apartment got tagged with “SLUT” graffiti. Unsurprisingly, now they’ve BOTH dumped his ass.

Honorable Mention: Certain celebs attract drama no matter who they’re dating. Here’s a special shout-out to Sienna Miller (remember Jude Law and Nannygate?); Anne Heche, whose splits with Ellen DeGeneres and Coley Laffoon were dramatic and bitter; and John Mayer, who’s never met a breakup he couldn’t use for attention, blog fodder, and/or PR. Jennifer Aniston, consider yourself warned.

Jen, Brangelina, and the Ten Worst Celebrity Breakups