Sean Penn & Robin Wright Penn
The Milk actor may have retracted his request for legal separation in May, calling it an "arrogant mistake" (Arrogant mistake? That doesn't sound very Sean Penn-y at all...), but it seems the on-again, off-again pair are really done for good. Robin Wright Penn filed for divorce on Aug. 12, revealing to More magazine that after 13 years of marriage, she's "too old for this s--t."
Kim Kardashian & Reggie Bush
The E! star and New Orleans Saints footballer reached their split amicably, citing poor timing as the cause for their "very sad" separation.
Joe Jonas & Camilla Belle
The cutie-pie couple called it quits right on the heels of the oldest JoBro's engagement. There's only one word for this split: :-(.
Eddie Cibrian & Brandi Glanville
Nearly four months after the rumors started that the actor had hooked up with his Northern Lights costar, LeAnn Rimes, his wife of seven years and the mother of their two sons revealed that they had "decided to take some time apart." Days after the announcement, buzz began to build that Rimes' marriage was also on the rocks. Cibrian made his split official (and unofficially confirmed his relationship with Rimes) by recently filing for divorce from Glanville.
Jessica Simpson & Tony Romo
Just weeks after her ex-hubby confirmed the end of his own rebound romance, Nick Lachey's Newlyweds costar called it quits with the Cowboys QB. (Coincidence?) At least the 29-year-old can always depend on her dog, Daisy.
Kim Cattrall & Alan Wyse
After five years together—and two decades apart (in age)—the Sex and the City star's chef BF packed up his knives when the romance cooled.
Nick Lachey & Vanessa Minnillo
This is worrisome...for event crews from L.A. to Miami who rely on the cute couple to hold red carpets in place. If the camera-friendly pair don't find pretty partners soon, the Crimson Floor Runners Guild will have to act fast.
Jon & Kate Gosselin
After dominating tabloids for months with tales of sordid affairs and child spanking, the parents of eight—sextuplets and twins—shocked absolutely no one when they filed for divorce. Married for 10 years, they discussed how this would affect their family privately on their TLC reality show.
Rachel Hunter & Jarrett Stoll
The NHL stud iced his engagement to the puck groupie seven weeks before their wedding day. Dude, that is just cold.
Jane Kaczmarek & Bradley Whitford
After 16 years of marriage and three children together, this couple called it quits. Once upon a time, back when Malcolm in the Middle and The West Wing were on the air and winning Emmys, these two were kind of a big deal on TV. But now, that's just a distant memory of good times past.
Miley Cyrus & Justin Gaston
The 16-year-old starlet ended her romance with the 20-year-old undies model after nine months of dating...and amid rumors that she was reuniting with ex Nick Jonas.
Lindsay Lohan & Samantha Ronson
The DJ seemed to exert a steadying influence on the trouble-prone actress before their tumultuous breakup this spring. At least LiLo wasn't admitted to rehab or arrested for DUI during their paparazzi-friendly relationship.
Rihanna & Chris Brown
Brown was charged with two felonies for allegedly assaulting his songbird girlfriend the night before the 2009 Grammy Awards. Although some reports have suggested the couple later reconciled, the "Umbrella" star was prepared to testify against her ex but he pleaded guilty to felony assault before she could do so. Brown was put on five years' probation and ordered to perform 180 days of community service.
Mel & Robyn Gibson
Married for 28 years and the parents of seven children, the pair seemed to have weathered the PR nightmare of his DUI arrest—but apparently not Mel's infidelity. The Oscar winner is now expecting his eighth child with girlfriend Oksana Grigorieva.
Kelly Rutherford & Daniel Giersch
The Gossip Girl star's own divorce rivals anything on her CW series—nasty headlines in the press, accusations of very bad behavior and a bitter custody battle. Plus, she just gave birth to their second child! Suddenly, Lily van der Woodsen's problems don't look so bad.
Amy Winehouse & Blake Fielder-Civil
A part of us died inside when England's storybook sweethearts announced their divorce plans. If a marriage falls apart after trifles like drug addiction, multiple arrests, incarceration, rehab, hospitalizations and infidelity, what hope is there for the rest of us?
Madonna & Guy Ritchie
Even if A-Rod and Madge really were just friends, it wasn't a huge shock when the Material Mom and the director announced their split after eight years together. Madonna blamed Guy's "unreasonable behavior" and denied a reported $76 million payout to the Sherlock Holmes helmer. No hard feelings, though: Ritchie called his ex a "fantastic and loving mother" in supporting her latest adoption bid.
Star Jones & Al Reynolds
Less than four years after one of the most lavish weddings in recent memory, the former View host filed for divorce after battling rumors of marital strife since 2006. In July, Reynolds admitted on YouTube that they're not on speaking terms.
Ryan Gosling & Rachel McAdams
The Canadian A-listers had been on and off since 2004, but they are decidedly off—at least for now. Some claim Rachel's controlling behavior prompted Ryan to break it off, while others simply pin the split on conflicting work schedules.
Téa Leoni & David Duchovny
Entering rehab for sex addiction doesn't sound wonderful for a marriage, and it proved too great for this 11-year union. The Californication star entered treatment in September, and a month later, reps for the couple confirmed they had been separated "for months."
Dylan McDermott & Shiva Rose
The Practice star quietly finalized his divorce from the Iranian actress this month after the under-the-radar couple separated a year earlier. Why the split after a dozen years married and two kids? He only cited the vague "irreconcilable differences" in court papers.
Anne Hathaway & Rafaello Follieri
Keeping up a long-distance relationship with a boyfriend in prison sounds pretty difficult, so we don't blame Anne for dumping the shady Italian businessman she dated for four years. She even gamely joked about the ordeal on SNL a month after he pleaded guilty.
Liv Tyler & Royston Langdon
The actress and rocker split in May amid rumors that she worried she married too young. (They got hitched in '03 when she was 25.) She later told U.K. Harper's Bazaar she was "feeling the pain" from breaking up with the father of her 4-year-old son, Milo.
Jimmy Kimmel & Sarah Silverman
After teasingly announcing in January that she is bleeping Matt Damon in a hilarious segment for Kimmel's show, the pair split for real in July after five years together. Then reunited. Then split again.