16 Wildest, Craziest Hollywood Marriages Ever (PHOTOS)

Zayda Rivera | Dec 31, 2015 Celebrities
16 Wildest, Craziest Hollywood Marriages Ever (PHOTOS)


Is it Hollywood that makes marriages crazy or is it that off-kilter people are attracted to Hollywood? Hmm, probably a little of both. Either way, when your marriage is subject to the paparazzi, confessional interviews, and memoirs, any hope that couples can keep their wild ways a secret for long is slim. 


Check out these 15 Hollywood marriages that made everyone drop their jaws at some point -- whether it was because the couple carried vials of each other's blood on them or became fugitives. Some of their stories are so outlandish they could easily be a blockbuster hit on the big screen. 



  • Pamela Anderson & Tommy Lee


    Image via RameyPix/Corbis

    Pamela Anderson and Tommy Lee's short but intense marriage, which lasted from 1995 to 1998, was pretty much a textbook rock-and-roll coupling: They married (she in a bikini) after knowing each other just 96 hours; there was an infamous sex tape, and a domestic violence incident that ultimately ended things. The pair, who have two sons,  twice failed to rekindle their romance. Though Anderson has married three more times, she recently said that Lee was her true love. "There was Tommy and then there was nobody else." 

  • Angelina Jolie & Billy Bob Thornton


    Image Via © Splash News/Corbis

    Before she was a mom of six, wife of Brad Pitt, and a roving humanitarian, Angelina Jolie married actor Billy Bob Thornton, who was 20 years older. Their mutual obsession was especially apparent when they began wearing vials of each other's blood -- and that was after they'd already graced us with seriously, ahem, over-the-top PDA. They divorced in in 2003 after three years of marriage.

  • Madonna & Sean Penn


    Image via 1997 Phil Ramey/RameyPix/Corbis

    The Material Girl was at her height when she married volatile bad boy Sean Penn, who once (at least) spit on and punched a photographer for snapping a picture of the couple. But their whirlwind marriage ended in 1989 after four short years. Rumors swirled for decades about an alleged incident in which Penn hit Madonna with a baseball bat and bound her, but the singer denied them in a 2015 court statement.

  • Randy & Evi Quaid


    Image via Peter Freed/Corbis

    A real life Bonnie and Clyde -- minus the dead bodies. Actor Randy Quaid and his wife Evi were arrested trying to cross back into the United States from Canada, where the couple had been living as fugitives, and posting increasingly incoherent Internet rants. The couple had had arrest warrants out since 2010 for squatting in their old California house and not paying hotel bills, but they claimed that "Hollywood star whackers" were after them. OK, then. 

    More from The Stir: 20 Male Hollywood Stars Who Married Regular People (PHOTOS)

  • Elizabeth Taylor & Richard Burton


    Image via Bob Penn/Sygma/Corbis

    Elizabeth Taylor was married eight times. Two of those times was to Richard Burton. Their romance was born amid scandal, as they met  met on the set of Cleopatra in 1963 -- while they were married to other people, and made no effort to hide their fling. They married a year later and divorced in 1974 amid claims of infidelity, but remarried just a year later before finally calling it quits in 1976. 

  • Frank Sinatra & Ava Gardner


    Image via Bettmann/Corbis

    Frank Sinatra left his wife for Ava Gardner, one of the biggest sex symbols in Hollywood, and married her in 1951. Although she called him the love of her life, Gardner ended up cheating on him. After two abortions and lots of booze and fighting, they ended their marriage in 1957. Sinatra and Gardner remained close for the rest of their lives. 

  • Ozzy & Sharon Osbourne


    Image via Ciao Hollywood/Splash News/Corbis

    They've been married for over three decades, so you know the love between Ozzy and Sharon Osbourne is real. But the The Talk host has had to put up with plenty from her rocker hubby, standing by Ozzy's side through multiple drug and alcohol addiction relapses and his attempt to strangle her while in an alcohol haze. "I regret trying to kill Sharon," he later said in an interview. "It wasn't my plan to go out, get p*ssed, try to strangle her and wake up in jail." We hope not.

  • Whitney Houston & Bobby Brown


    Image via Splash News/Splash News/Corbis

    When Whitney Houston and Bobby Brown first got together everyone warned her about the R&B party boy's reputation. But it turns out they were a bad influence on each other. The couple quickly became known for their drug use and enabling each other's addiction. Houston, who was once looked at as a wholesome, admitted to smoking crack and using other drugs with Brown. She died in 2012 due a drug overdose after being found unconcious in a bathtub. Sadly, their daughter Bobbi Kristina followed suit, in the same manner, in 2015. 

    More from The Stir: 21 Female Hollywood Stars Who Married Regular People (PHOTOS)

  • Amy Winehouse & Blake Fielder-Civil


    Image via Jean Catuffe/INFphoto.com/Corbis

    As English singer Amy Winehouse delved deeper into drug use, fans blamed husband Blake Fielder-Civil, who had a history of heroin use, for her very public downward spiral. Their relationship seemed to survive criticism and his stint in jail, but Fielder-Civil filed for divorce in 2009 and she died of alcohol poisoning in 2011, at age 27. In an interview ahead of the release of the documentary Amy, he rejected claims that he's responsible for her death, saying the were both "lost and damaged souls."

  • Tiger Woods & Elin Nordegren


    Image via RameyPix/Corbis

    Their relationship seemed perfect to the untrained eye, but after a fateful Thanksgiving weekend in 2009, Tiger Woods and Elin Nordegren's marriage exploded. After learning he'd cheated on her, Nordegren threw a cell phone at Woods, chipping his tooth, and then chased him out of the house with a golf club, smashing two windows of his Escalade. They divorced in 2010 after he was further exposed -- as a serial cheater. 

  • Khloe Kardashian & Lamar Odom


    Image via Splash News/Splash News/Corbis

    Khloe Kardashian and Lamar Odom had a passionate four-year marriage that crumbled due to his substance abuse. Although she's moved on and had other relationships, Kardashian rushed to Odom's side this year after he was found unconcious in a Nevada brothel following a drug binge. Since their divorce has not been finalized she was in charge of making medical decisions for the former NBA player, who survived multiple strokes. Odom remains in recovery with Kardashian one of his biggest supporters. The future of their marriage hangs in the balance. 

  • Charlie Sheen & Denise Richards


    Image via Fred Prouser/Reuters/Corbis

    Talk about a toxic relationship. Charlie Sheen and Denise Richards were married for four years before their nasty divorce exposed the hell that their marriage apparently was. In divorce papers, Richards called Sheen an unstable, abusive, and violent man addicted to gambling, porn, and prostitutes. She alleged he even threatened to kill her. The two have since patched up their relationship as co-parents, with Richards even keeping his biggest secret: his HIV-positive status. 

    More from The Stir: 22 Hollywood Marriages That Have Lasted More Than 10 Years (PHOTOS)

  • Britney Spears & Kevin Federline


    Image via Katy Winn/Corbis

    Britney Spears quickly fell into a spell when she met former background dancer Kevin Federline. They married in 2004 shortly after meeting -- while his on-and-off girlfriend was pregnant with their second child. Three years, two sons, one gross-out reality show, and about 200 parenting fails later, they were done. Spears went through a very public meltdown in 2007, the same year their marriage ended. At one point she even shaved her head and was photographed going berserk on a paparrazi's car with an umbrella. 

  • Tilda Swinton & Sandro Kopp


    Image via Splash News

    OK, they are not married, but Tilda Swinton's relationship with and longtime partner Sandro Kopp became wildly intriguing when she indicated they shared a home with her ex and the father of her children, John Byrne. Still, the actress shot down rumors of a polyamorous lifestyle. While both men remain present in Swinton's life she insists it isn't the supposed ménage à trois she's reportedly living. 

  • Cary Grant & Dyan Cannon


    Image via Bettmann/Corbis

    By the time classic Hollywood star Cary Grant married actress Dyan Cannon, who was 33 years his junior, in 1965, gay rumors about him were rampant. But it was his experimental drug use that set her hair on end. In her 2011 autobiography, Cannon claimed that Grant practically forced her to take LSD, leading to her epic freak out, in which she hallucinated that the walls were breathing, that dancing bears were singing in German, and that Grant was turning into an old man in front of her eyes. She soon afterward experienced a nervous breakdown and the couple divorced in 1968.

  • Kurt Cobain & Courtney Love


    Image via Fred Prouser/Reuters/Corbis

    The documentary Montage of Heck, which centered around Nirvana rocker Kurt Cobain, revealed much about his marriage to Courtney Love. Grainy home videos show the couple indulging in heroin inside their filthy home-turned-drug-den, where their daughter Frances Bean also lived. But contrary to popular belief, it wasn't Love who got Cobain, who later committed suicide, addicted. Rather, she started using again when they got together, since being a junkie was one of his stated goals. So sad.

    More from The Stir: 20 of The Shortest Hollywood Marriages Ever (PHOTOS)

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