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Sean Penn slowly shed his bad-boy image throughout the 1990s, and his marriage following a long courtship to actress Robin Wright in 1996 solidified his toned-down attitude. Despite having two children together and a period of apparent calm for roughly a decade, the couple grew apart in the late 2000s—fueled in part by rampant rumors of an affair between Penn and Natalie Portman—and finally split for good this past summer. (Photo by Jason Merritt/Getty Images) See the full story at The Daily Beast
Sean Penn slowly shed his bad-boy image throughout the 1990s, and his marriage following a long courtship to actress Robin Wright in 1996 solidified his toned-down attitude. Despite having two children together and a period of apparent calm for roughly a decade, the couple grew apart in the late 2000s—fueled in part by rampant rumors of an affair between Penn and Natalie Portman—and finally split for good this past summer. (Photo by Jason Merritt/Getty Images) See the full story at The Daily Beast
The Hills stars have had a good portion of their relationship televised, which makes for ample evidence of dysfunction. The couple was surreptitiously married in 2008, reneged on a divorce announcement in September, and reportedly have a friendly relationship with Mary Jane. Oh, and while they were "split," Pratt was shopping around a sex tape. Montag and Pratt reconciled last month and burned their divorce papers in front of a gaggle of photographers. (Photo by David Becker/Getty Images) See the full story at The Daily Beast
She of the Grizzly Bear momma and he of the Playgirl spread, Bristol and Levi got together way back in his freshman year of high school. America's favorite young Republicans had a child together in December 2008, and while Bristol has kept a relatively low profile (Dancing with the Stars gig aside), things got weird for Levi after the couple split in 2009. He dove headfirst into the media vortex, giving nationally televised interviews criticizing the Palins and posing in Playgirl. Bristol and Levi announced they were back together in July 2010, but by August they were kaput again after Levi told Bristol there was a chance he'd fathered another child with another teenager. (AP Photo/Paul Sancya) See the full story at The Daily Beast
The relationship between Marshall and Kim is perhaps best described in song. To wit, from Eminem's "Kim": "Sit down, bitch, I'll beat the shit out of you." As far as anyone can tell, Em's artistic threats of physical violence never materialized, but that didn't stop the tabloid fodder. Things got so bad public relations-wise that Kim attempted suicide in 2000 and sued Eminem for $10 million. They were remarried in January 2006, but three months later Eminem re-ended the relationship. (Photos by Bill Pugliano and Frederick M. Brown/Getty Images) See the full story at The Daily Beast
These two had it all before they were even old enough to drink—multimillion-dollar recording contracts, sports cars, media adoration, and worldwide fame. Then, an argument in Chris Brown's Lamborghini before the 2009 Grammy Awards erupted into a vicious beating—disturbing pictures of the aftermath of Rihanna's broken face were plastered across Internet gossip sites. Brown's image was forever altered, but Rihanna has bounced back. "I needed that wake-up call in my life. That was the only way I would have gotten out of that relationship," she said in the December issue of Marie Claire magazine. (Photo by Scott Gries/Getty Images)See the full story at The Daily Beast
Ah, how the tides have turned. Jon and Kate met at a company picnic in 1997 and married in 1999, eventually giving birth to eight kids. Their lives were documented on the TLC reality series Jon and Kate Plus 8, with Jon playing the role of the doting, loving father, and Kate the bossy control freak. Allegations swirled that Jon was having an affair in March 2009, when he was caught sneaking out at night with Deanna Hummel, a third-grade teacher. The couple filed for divorce on June 22, 2009, with Kate keeping the family home and primary custody of all eight kids. Following their split, the two have embarked on contrasting career paths. Jon fell in love with club nightlife—and Ed Hardy clothing—dated a string of questionable younger women, and is reportedly going broke, while Kate appeared on Dancing with the Stars and is the star of her own TLC reality show, Kate Plus 8. (Photo by Thos Robinson/Getty Images for Discovery) See the full story at The Daily Beast
The suspendered, septuagenarian host of CNN's Larry King Live has tied the knot a whopping eight times to seven different women. His most recent nuptials were on Sept, 5, 1997, when he married former singer and Playboy bunny Shawn Southwick. Shawn and Larry had two children—Chance and Cannon— but things got dicey in 2007, when the couple had a very public screaming match outside a Beverly Hills eatery, and Southwick eventually checked into rehab for an eating disorder, with sources citing Larry's controlling attitude as the cause. On April 14, 2010, both King and Southwick filed for divorce, with Southwick accusing King of having an affair with her younger sister, Shannon Engemann, and King alleging that Southwick had an affair in 2008 with their son's baseball coach. The two lovebirds reconciled in May. (Photo by Evan Agostini/Getty Images) See the full story at The Daily Beast
Bullock arranged for her 10-year-old godson to meet James as a Christmas gift, and the two hit it off. The leading lady married the motorcycle builder on July 16, 2005. Things seemed peachy for the couple, who formed a united front battling James's ex, porn star Janine Lindemulder, in a custody battle over James's daughter in late 2009, emerging victorious. However, just over a week after Bullock won the Best Actress Oscar for her performance in The Blind Side, Bullock pulled out of her European promotional tour of the film when Michelle "Bombshell" McGee, a tattoo model-stripper-former white supremacist, came forward alleging that she and James had an 11-month affair while Bullock was on location filming The Blind Side. James eventually checked into rehab for drugs, alcohol, and sex addiction, while Bullock went through with her and James's previous plans to adopt a baby boy, Louis, from New Orleans. Bullock filed for divorce in April 2010, and it came to light that James had as many as five mistresses. (Photo by Pascal Le Segretain/Getty Images) See the full story at The Daily Beast
This was one kooky couple. The Oscar-winning actress and the plastic surgery-loving concert promoter were married in an over-the-top ceremony on March 16, 2002—with Elizabeth Taylor serving as maid of honor and none other than the late Michael Jackson carrying the bride's train. However, the two parted ways less than a year and a half later, in July 2003. And then things got strange. In October 2003 Gest, known for gag-inducing acts of PDA with Minnelli, filed a $10 million lawsuit against her, alleging that the Cabaret star beat him so badly during alcoholic rages that she caused permanent nerve damage. Minnelli then countersued, claiming Gest stole up to $2 million from her while they were together. They ultimately settled with each other and agreed to a no-fault divorce on Jan. 18, 2007. (AP Photo/Sang Tan) See the full story at The Daily Beast
Theirs was a union marred by tragedy. Stern first crossed paths with Smith when his law firm handled her modeling contracts in the early 1990s, and again when Smith fought with the sons of her late husband, J. Howard Marshall, over the octogenarian's fortune. Stern soon left his law firm to become Smith's agent of sorts, co-starring with her on The Anna Nicole Show. The two eventually became romantically involved, and when Smith had a daughter, Dannielynn Hope Marshall Stern, on Sept. 7, 2006, the birth certificate recorded the father as Howard K. Stern. The couple exchanged vows in a non-legally binding ceremony on a boat near Nassau a few weeks later. After Anna Nicole Smith died from a drug overdose on Feb. 8, 2007, Stern was initially granted custody of Dannielynn, until it was revealed following a long paternity case that photographer Larry Birkhead was the biological father. Oh, and it got worse. Stern, along with doctors Sandeep Kapoor and Khristine Eroshevich, were charged with prescribing and administering drugs to Smith. Stern and Eroshevich were both found guilty of the charges on Oct. 28, 2010, according to CNN, with each facing up to three years in prison. (Photo by Amanda Edwards/Getty Images) See the full story at The Daily Beast
The relationship between LiLo and SamRo was a tabloid romance made in heaven. The starlet and the celebrity DJ became a couple in spring 2008, but after a year on-and-off they finally called it quits last year. Lindsay revealed that the fling was "passionate" but that Ronson's famous family may have played a part in its demise, saying, "There have been a lot of ups and downs. Her family is very involved in her relationships and that was difficult." Anonymous sources have leaked that SamRo and Lilo's relationship could be back on the front burner. (Photo by Chris Jackson/Getty Images for Atlantis, The Palm) See the full story at The Daily Beast
Nicknamed the "Sid and Nancy" of their generation, Amy Winehouse and Blake Fielder-Civil have been through it all: drug addiction, rehab, marriage, divorce, cheating allegations, and assault charges. The two were married in 2007, but were photographed soon after in London bruised and bleeding. Months later Winehouse was hospitalized for a drug overdose, and soon after the couple was arrested in Norway for marijuana possession. Winehouse later said of the union with Fielder-Civil: "Our whole marriage was based on doing drugs." The split was finalized in 2009. (Photo by Dave Hogan/Getty Images) See the full story at The Daily Beast
Age hasn't subdued the antics of Charlie Sheen. He made headlines 20 years ago for accidently shooting fiancée Kelly Preston in the arm (she subsequently ended the relationship). Of course, his former wife Denise Richards has publicly accused him of drug abuse and threatening behavior. His third, and most recent, marriage to Brooke Mueller lasted just over a year, ending in a violent fight on Christmas Eve in 2009, with Mueller alleging that he pulled a knife on her during a 911 call. (Photo by Ethan Miller/Getty Images for BASE Entertainment) See the full story at The Daily Beast
During his career as a Hollywood A-lister, Mel Gibson survived accusations of homophobia and anti-Semitism, but nothing came close to the level of controversy that was sparked by the release of phone conversations between him and girlfriend Oksana. In the leaked recordings, Gibson threatened to kill the Russian singer and burn down her house. Dueling restraining orders were filed, and authorities launched an investigation into allegations of spousal abuse by Gibson. (Photo by Angela Weiss/Getty Images) See the full story at The Daily Beast
The romance between Britney and her boytoy backup dancer started fast: Three months after they met, the couple was engaged. There was drama from the start, including the pregnancy of Federline's ex, actress Shar Jackson, and the television reality show chronicling their newlywed bliss. But after just two years of marriage, the couple filed for divorce. Nearly a year of legal battles later, Federline ended up with custody of sons Jayden and Sean and a reported $20,000 in monthly spousal support. (AP Photo/Danny Moloshok) See the full story at The Daily Beast
Though his divorce from Brooke Mueller has been garnering headlines lately, the Plaza Hotel's least favorite guest, Charlie Sheen, and his relationship with second wife, Denise Richards, did not fare well either. He was married to the former Bond girl from 2002 to 2005 and the couple had two daughters together. But in March 2005, while she was still pregnant with their second child, Richards filed for divorce, citing "irreconcilable differences." She accused her now ex-husband of abusing drugs and alcohol, as well as being "unstable, violent, addicted to gambling and prostitutes, and visit[ing] pornographic web sites featuring young men and girls who appear underage," The Smoking Gun reported. Though he denied any allegations of extramarital affairs, the abuse allegations were enough to get Richards a restraining order against her estranged husband in 2006, requiring him to stay at least 300 yards away from his ex-wife and their two daughters, except for supervised visits. (Photo by Kevin Winter/Getty Images) See the full story at The Daily Beast
The "I Will Always Love You" singer and New Edition boy band member met at the 1989 Soul Train Music Awards. They wed three years later and welcomed their first and only child together, Bobbi Kristina, in 1993. After an airport pot scandal and a struggling music career sent Houston and Brown down to train-wreck status, they signed on to exploit themselves on Bravo's 2005 series Being Bobby Brown. But it wasn't enough to save their careers or their marriage—in 2006, the couple filed for divorce. After their separation was legally finalized, Brown sued Houston to change the terms of their custody agreement. Later, when she gave her first public interview in nine years to Oprah in 2009, Houston admitted that Brown was emotionally but not physically abusive—though she did cite one instance in which she claims he spit on her. "Holy matrimony was a very serious thing for me. I was going to keep my vow. I never cheated," she told Oprah. "The only thing I did was the drugs…He was too promiscuous, dragging dirt into my home. It disturbed me." The songstress was apparently referring to the self-proclaimed "Video Vixen" Karrine Steffans, with whom Brown reportedly became involved before divorcing Houston—because that's his prerogative. (Photo by Amanda Edwards/Getty Images) See the full story at The Daily Beast
What began at an event for animal rights and charity unraveled into one of the messiest, most expensive divorces in Hollywood history. Four years after wife Linda McCartney died of breast cancer, Sir Paul married former model Heather Mills in Ireland in 2002. A year later they welcomed Beatrice Milly McCartney, but the two couldn't maintain their initial spark. They separated in 2006, and Mills began making public appearances lambasting McCartney's daughter, fashion designer Stella, and accusing McCartney of drinking too much alcohol, smoking too much marijuana, and abusing her on three occasions—stabbing her with a broken wine glass, shoving her onto a table, and pushing her into a bathtub while she was pregnant, according to The Mirror. Mills, who reportedly cheated on McCartney, represented herself in court and was awarded nearly $50 million in 2008—not a bad haul, but quite the tumble from the rumored $1 billion that McCartney's worth. (Photo by Frazer Harrison/Getty Images) See the full story at The Daily Beast
The number of times Jersey Shore's token "sweetheart," Sammi Giancola, has shouted, "I'm done!" at her on-again-off-again boyfriend, Ronnie Ortiz-Magro, also seems to correspond to the number of times the couple has gotten back together. Their perma-tanned, tumultuous on-air romance blossomed in the MTV series' inaugural season, and drama soon followed. From calling her a bitch to remarks about her "Fred Flintstone toe," Ronnie's comments have led to massive blowout fights. But the verbal abuse turned physical when Ortiz-Magro pushed Giancola on the boardwalk and "traumatized" her during a January episode. Though he apologized and they reconciled, Sammi and Ronnie broke up again on-air during the first season's reunion episode, when never-before-seen footage revealed that Giancola flirted with other men while the two were together. When season two began, Ortiz-Magro retaliated by creeping with numerous grenades (some at the same time) while at clubs and then getting into Giancola's bed later that night. Though countless fights followed and her roommates tried to dissuade her from Ronnie's gorilla embraces, as of the season two reunion, the two are still together and Ortiz-Magro admitted, "I did a lot of messed up things." (Photo by Jason Merrittand avid Livingston/Getty Images) See the full story at The Daily Beast
The tale of the Swedish au pair and world championship golfer did not end happily. After a sunset wedding in Barbados, two children, and a suspicious Thanksgiving single-car accident, the union of Tiger Woods and Elin Nordegren quickly unraveled all over the covers of tabloids. Nearly a month after an incident involving his smashed SUV and a golf club, Woods admitted to his infidelity after multiple women—prompted by nightclub promoter Rachel Uchitel—revealed their alleged intimate involvement with the athlete. The National Enquirer reported that the disgraced golfer acknowledged cheating on Nordegren with at least 120 women. "I was unfaithful. I had affairs. I cheated. What I did is not acceptable, and I am the only person to blame," he said in a statement before reportedly heading off to a rehab facility for sex addiction. For months afterward, the allegations surrounding Woods' extramarital affairs dominated headlines, until their $100 million divorce was finalized. (Photo by Andrew Redington/Getty Images) See the full story at The Daily Beast
