Doomed Couples

As Bristol Palin and Levi Johnston reunite, Shushannah Walshe talked to Ben Barber, the boyfriend Bristol just broke up with, about Levi’s failings and Bristol’s pregnancy rumors.

Jason LaVeris

Jason LaVeris

Jesse James and Kat Von D

When Michelle “Bombshell” McGee announced her alleged affair with Jesse James, igniting the deterioration of his marriage to Sandra Bullock, many were struck by the heavily-tattooed model’s anti-girl-next-door appearance. But just two months after the Bullock and James’ divorce was finalized in June, he stepped out with a McGee look-a-like: TLC reality star, Kat Von D. The 28-year-old L.A. Ink tattoo artist soon confirmed their relationship via Twitter. A month later, she told People that 41-year-old James was “The One,” a notion she came to realize over a game of Scrabble one day. “Jesse is only my ninth boyfriend. I don't hang out with anybody unless I am in love,” Von D said.  And James apparently felt the same, announcing Thursday that he proposed and she accepted. This will be James’ fourth marriage and a first for Von D, who most recently dated Mötley Crüe’s 52-year-old bassist Nikki Sixx.  “2010 was actually the best year of my life because I fell in love with my best friend," James exclusively told People. "Growing old with her is going to be a f------ blast!" If they make it that long…


Chuck Kennedy, MCT / Landov

Bristol Palin and Levi Johnston

Bristol Palin stunned the world--and apparently even her own mother, Sarah Palin--when she announced her engagement to ex-boyfriend Levi Johnston on the cover of Us Weekly in July. In August, it was off again. The couple has a rocky history, including MySpace drama with Johnston's mother and sister, and tension over his Playgirl photo shoot. But during the pair's previous engagement in 2008 when they announced Palin's pregnancy, Johnston assured the press that their love was real. "We were a long time ago with or without the kid," he told the Associated Press. "That was the plan from the start." Palin and Johnston are raising their son Tripp together. In happier days, when he lost a ring Palin had given him on a caribou hunt, he decided to tattoo her name on his finger instead.

AP Photo

Lisa Marie Presley and Michael Jackson

The news that the King of Pop had married the daughter of the King of Rock 'N' Roll was seemingly a musical fairy tale too good to be true. And in fact, even though Presley’s mother Priscilla allegedly gave her blessing, the marriage didn’t last, ending just 18 months after it began. The validity of their marriage has often been questioned, especially given the timing of their nuptials, which coincided with Jackson’s investigation for child-abuse charges. However, Presley has publicly stated that their marriage was legitimate and that she truly loved him. After Jackson’s death in the summer of 2009, Presley shared her surprise and pain on her MySpace blog and once again, came to the defense of their union. "Our relationship was not 'a sham' as is being reported in the press," she wrote. "It was an unusual relationship, yes, where two unusual people who did not live or know a 'normal life' found a connection, perhaps with some suspect timing on his part. Nonetheless, I do believe he loved me as much as he could love anyone and I loved him very much."


Angelina Jolie and Billy Bob Thornton

The frightening marriage between Angelina Jolie and Billy Bob Thornton began in 2000, when the pair, who met on the set of Pushing Tin eloped. Seemingly, Thornton, who is years Jolie’s senior, enjoyed the spotlight just as much as his wife did. The couple regaled the media with details of their personal lives. "I wear her underwear a lot when we're away. And she wears mine," Thornton told Entertainment Tonight on one occasion, for example. And let’s not forget that they wore vials containing each other’s blood around their necks. Jolie also reportedly bought her husband a grave plot in celebration of their anniversary. But attention-garnering quirkiness and a fascination with all things morbid was not enough to sustain their relationship, as they ultimately decided to split up. Jolie told Barbara Walters, "He started focusing on certain things, his music, and different films… I started focusing on traveling a lot… and really wanted to adopt a child… Billy and I just became very different people, and that was before Maddox even came home. And, by the time Maddox came home, we were kind of living apart."

UPI / Landov; AP Photo

Britney Spears and Jason Alexander

Little did we know that getting hitched on a whim in Las Vegas would be one of Britney Spears' least eyebrow-raising antics. In 2004, the pop princess and her childhood friend Jason Alexander (who never appeared as George Costanza on Seinfeld) tied the knot at 5:30 a.m. at the Little White Wedding Chapel on the Vegas Strip after a night of clubbing. According to Spears' attorney, the singer was " absolutely not" drunk at the time. "It was just crazy, man," Alexander, who was then a junior at Southeastern Louisiana University, told Access Hollywood. "And we were just looking at each other and said, 'Let’s do something wild, crazy. Let’s go get married, just for the hell of it."’ The two were husband and wife for a whopping 55 hours, before having their marriage annulled. The annulment petition read, "Plaintiff Spears lacked understanding of her actions to the extent that she was incapable of agreeing to the marriage."

AP Photo

Liza Minnelli and David Gest

Who would have guessed after an elaborate $3.5 million wedding in 2002 that things would go so horribly wrong for Liza Minnelli and David Gest? Actually, many people, as it turns out. Minnelli said later she asked Michael Jackson, "Why did you let me marry this idiot?" And considering he also made our list, it’s probably not a good sign. The 16-month marriage quickly turned sour: Gest, who was Minnelli’s manager, immediately established an ambitious course for his new wife with a tour called "Liza’s Back" and an accompanying diet of 900 calories per day, The Daily Mail reported. When Minnelli announced she would be spending their first anniversary in detox, there was little surprise when the divorce announcement came only four months later. A very nasty split played out in the media in the preceding months. Some speculated Gest—who has fended off rumors about being gay—only married Minnelli for her money, a claim that seemed substantiated by the rumor that he attempted to win $10 million from her in their divorce settlement. Gest allegedly also said their prenup was invalid because she gave him herpes and allegedly assaulted him. After both sides dropped their lawsuits, Gest and Minnelli finalized their dirty divorce in 2007, five years after the unbelievable union began.

Chris Polk / AP Photo

Ben Affleck and Jennifer Lopez

The infamous film Gigli wasn't Bennifer's only doomed collaboration. Shortly after her marriage to backup dancer Cris Judd ended in 2002, Lopez upgraded to Oscar-winner Ben Affleck and not a moment of their relationship was free from public scrutiny. The pair got engaged in 2003, but called off the wedding in the eleventh hour. Lopez later told Graham Norton, "It was a lot for both of us to be under that type of siege for two years straight... the media latches on to certain things... and our relationship did suffer because of that." But she was quick to add that the media was "not the only reason." Affleck agreed with Lopez’s assessment, saying, "I think Jen and I made a mistake in that we fell in love, we were excited and maybe too accessible. I don’t think either of us anticipated the degree to which it would take on a world of its own." It wasn't a total loss, however—the couple gave us one of the inaugural celebrity couple portmanteaus.

Paul Smith, Featureflash / Retna

Ellen DeGeneres and Anne Heche

Hollywood's most famous same-sex couple got together the same year Ellen DeGeneres came out of the closet on her eponymous sitcom in 1997. The couple's adoration and love for one another was constantly on display throughout their incredibly high-profile relationship, the most prominent of its kind at that point. In 2000, just a few months before their three-and-a-half year relationship ended, DeGeneres told reporters, "It’s a celebration every single day... It’s kind of disgusting and crazy that we’re like…’Oh, we’re so lucky.’" Soon enough, however, tabloids broke the news their luck had run out. "Unfortunately, we have decided to end our relationship," the two said in a statement. "It is an amicable parting, and we greatly value the three and a half years we have spent together. We hope everyone will respect our privacy through this difficult time." Shortly after the split, Heche stumbled into a stranger's Los Angeles apartment, announced she was the reincarnation of God and spoke of the coming of her alien friends. As DeGeneres previously insinuated, crazy was clearly involved in their relationship.

Robin Platzer, Twin Images / Getty Images

Macaulay Culkin and Rachel Miner

Macaulay Culkin was no longer home alone at age 17, after he and his also 17-year-old girlfriend, actress Rachel Miner, married in an intimate ceremony in Connecticut in 1998. Sadly, the young couple separated two years later and finally divorced in 2002. Even though they were "thrilled to have found each other as soul mates at such a tender age," which they announced in a public statement, and were looking "forward to spending [their] lives together," the pair unfortunately discovered that "soul mates" discovered at that "tender age" are not so likely to last.

Bill Davila / Retna Ltd.

Julia Roberts and Lyle Lovett

Julia Roberts and Lyle Lovett’s shotgun wedding shocked everyone—they’d only known each other a few weeks when they surprised the town of Marion, Indiana, with their impromptu church wedding. Although none of their friends had known of the affair, everyone reported that the two were absolutely in love. Romantic details soon came out, such as Grammy-winner Lovett picking out her wedding dress, (which she wore barefoot to the ceremony) and Roberts knitting him a sweater. But, despite their purported love, tested by all of three weeks of courtship, the two didn’t make it. The pair’s respectively hectic work schedules kept them more apart than together. In the end, the couple divorced quietly and amicably, announcing the split with a simple statement, "We remain close and in great support of each other."

AP Photos

Charlie Sheen and All Wives

Maybe Brooke Mueller hoped she would be different than Charlie Sheen’s previous two wives, but her marriage to Sheen seemed all too familiar. His marriage to Donna Peale in 1995 lasted less than a year, but the real lesson for Mueller should have come from his second ex-wife, Denise Richards. Sheen and the Wild Things actress married in 2002, but Richards left him three years later while pregnant with their second child. Their ensuing divorce and custody battle lasted for years before than finally settled in 2008, just before he married Mueller. Mueller and Sheen married that same year and she gave birth to twin sons in 2009, but their marriage soon hit the rocks. On Christmas Day, Sheen was arrested for allegedly threatening Mueller with a knife, and by June 2010, they signed divorce papers. The divorce papers reportedly specifically said Sheen could not go public with information about Mueller’s alleged drug use and Mueller could not go public about Sheen’s alleged cheating and drug use. Even if marriages aren’t, some things are still sacred.

Enfoque / Sipa

Renee Zellweger and Kenny Chesney

Only one week after letting the public know about their romance, actress Renee Zellweger and country singer Kenny Chesney were married in a private ceremony in St. John, Virgin Islands in April 2005. The pair had started dating in January 2005, but things turned sour almost as quickly as they started: In September, Zellweger filed for an annulment, citing "fraud." Although rumors about Chesney’s sexual orientation began to surface, the couple released a joint statement saying, "Miscommunication of the objective of their marriage at the start is the only reason for this annulment." Zellweger maintained that the marriage was the " biggest personal mistake of [her] life." and Chesney later told Oprah Winfrey he "panicked" about being married and he "felt that marriage made me lose my identity." At least they agreed on that.

Kevin Winter / Getty Images

Pamela Anderson and Kid Rock

Pamela Anderson announced her divorce from Kid Rock with the following message: "Divorce. Yes, it’s true. Unfortunately impossible." But it was seemingly possible, since the couple signed divorce papers shortly thereafter. The Baywatch star and rocker married first on July 29, 2006, then wed legally on August 3 at a Beverly Hills courthouse, and later, held a third, surprise ceremony on August 17 onstage in Nashville. But the couple—who had called off a previous engagement—were not meant to be: They filed for divorce by Thanksgiving. Although Anderson and Kid Rock cited "irreconcilable differences" as the reason for the split, rumors swirled that they got in an argument at the premiere of Borat, where she had a small cameo that he insisted he knew nothing about. Is it possible Borat was responsible for their breakup? After all, the man who played him and wore a neon banana hammock in the process has managed to keep his marriage together.

Andrew D. Bernstein / NBAE via Getty Images

Madonna and Dennis Rodman

The relationship between queen of pop Madonna and NBA baller and tattoo enthusiast Dennis Rodman was odd and fleeting. The two got together briefly in 1994, but despite possibilities of wardrobe sharing, it did not last. Madonna was modest about Rodman's appeal: "I love Dennis Rodman. He's hot. I adore him. He's a rebel, the Madonna of the NBA," she told USA Today. Rodman contends that Madge booty-called him while he was in Las Vegas, in a desperate attempt to have a baby. "So I left my chips on the table, flew five hours to New York and did my thing. We got done and she was standing on her head in an attempt to promote conception—just like any girl trying to get pregnant," Rodman wrote. "I flew back to Las Vegas and picked up my game where I left off." Though the conception and relationship both didn’t work, Madonna eventually did get pregnant, no thanks to Rodman.