20 of the Worst Celebrity Couples of All Time

Nicole Pomarico | Jul 18, 2019 Celebrities
20 of the Worst Celebrity Couples of All Time
Image: KMazur/WireImage/Getty Images

Nick Lachey and Jessica Simpson
KMazur/WireImage/Getty Images

Trying to hold down a relationship or marriage in Hollywood isn't easy. Sometimes, it goes seriously wrong. Although there are certainly plenty of celebrity relationships that are total #goals, what about the ones that aren't? The ones that have had us seriously concerned for the people involved? There are plenty of those, too -- maybe even more than the good ones. Through the years, a lot of these celebrity couples have gone down in flames, and one of the consequences of living in the spotlight is that the rest of the world got to see it all happen, usually in real time.

Unfortunately, the way that a lot of celeb relationships go wrong is the same way relationships go wrong for everyone -- just on a much larger scale, since the whole world is watching. Things like infidelity and growing in two wildly different directions are just as likely to break up celebrities as they do regular couples. But in some cases, these couples are also dealing with scary stuff, like abuse and drug addiction.

For most of these couples, things going wrong seemed to signal the end -- like when Ashton Kutcher and Demi Moore finally agreed they shouldn't stay together and went their separate ways. But in the case of other couples -- like Tori Spelling and Dean McDermott -- they've chosen to make it work, even though they've had to overcome some seriously huge obstacles along the way.

Recently, Cheatsheet rounded up the worst celebrity couples of all time, and it's really taken us on a walk down memory lane. Read on for some of the most volatile and turbulent relationships that Hollywood has ever seen. Maybe it's for the best that most of these have already ended ...

  • 20. Elizabeth Taylor & Richard Burton

    Richard Burton, Elizabeth Taylor
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    Elizabeth Taylor and Richard Burton's marriage is legendary for how turbulent it was. After all, they did divorce only to get married again. When they fell in love the first time, they were both married to other people, and according to Woman's Day, at the time, Elizabeth was known for having tantrums, and Richard was reportedly an alcoholic. Their second marriage didn't last long, because of how frequently they fought.

  • 19. Courtney Love & Kurt Cobain

    Kurt Cobain, Courtney Love, Frances Bean Cobain
    Miranda Shen/Fotos International/Getty Images

    Kurt and Courtney's volatile relationship began in the early '90s. When things began, Courtney told Vanity Fair that a lot of drugs were involved.

    "We went on a binge," she said in 1992. "We did a lot of drugs. We got pills and then we went down to Alphabet City and Kurt wore a hat, I wore a hat, and we copped some dope. Then we got high and went to SNL. After that, I did heroin for a couple of months."

    They did try to get clean for the sake of their daughter, Frances Bean, but ultimately, Kurt ended up dying from a self-inflicted gunshot wound in 1994, just two years after he and Courtney were married.

    So tragic.
  • 18. Anjelica Huston & Jack Nicholson

    Anjelica Huston, Jack Nicholson
    Splash News

    In her memoir, Watch Me, Anjelica opened up about how she'd caught Jack cheating on her during their 17-year relationship (she found items belonging to other women in their home). She had also told Jack that she'd wanted to get married, but he brushed off the idea. Finally, it ended when one of the women he was seeing became pregnant.

  • 17. Ozzy & Sharon Osbourne

    Ozzy Osbourne, Sharon Osbourne
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    Even though they've chosen to stay together through it all, Sharon and Ozzy's relationship has been a rocky one. Not only did Ozzy cheat on Sharon with multiple women, but in 2018, she admitted in an interview with The Sun that she had drugged him to get him to confess.

    "I was a broken woman," she said. "He sent me an email that was meant for one of his women. Then he took his sleeping pills. I put an extra two in his drink and asked him everything, and everything came out."

  • 16. Lindsay Lohan & Samantha Ronson

    Lindsay Lohan, Samantha Ronson
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    Lindsay Lohan and Samantha made headlines during their relationship, which went down in flames in 2009. Videos of their dramatic fights even hit the internet -- including this one from X17, where they tearfully fought outside of Samantha's home. Then, in a tweet, Lindsay accused Samantha of cheating on her

    "Being cheated on does wonders to you. I'm doing this publicly because u&ur friends call People [magazine]. So you win, you broke my heart. Now go away. I loved you," she tweeted, adding, "PLEASE leave me ALONE. and stop staying in the room below me, you've woken me and my mother up. go to bed. keep cheating u win."

  • 15. OJ Simpson & Nicole Brown Simpson

    OJ Simpson, Nicole Brown Simpson
    Rose Hartman/Getty Images

    OJ and Nicole's relationship is famous for the murder trial that ensued after she was found dead. Ultimately, OJ was found not guilty, but people have their doubts. However, the trial did reveal that OJ had abused Nicole, with graphic photos of her injuries shared for all to see.

  • 14. Jesse James & Sandra Bullock

    Jesse James, Sandra Bullock
    Splash News

    Jesse and Sandra Bullock's almost five-year marriage went down in flames when the world found out that he'd cheated on her with multiple women. And as of 2017, it sounds like he still doesn't think it's such a big deal.

    "In general, both women and men cheat ... It's part of life," he told The Daily Mail at the time.

    Uh, we have a feeling that Sandra would disagree ...
  • 13. Tori Spelling & Dean McDermott

    Tori Spelling, Dean McDermott
    Image Press/Splash News

    Tori and Dean have had a pretty rocky relationship ... and all the ups and downs of their more than 10-year marriage have been broadcast for the world to see, thanks to their reality stardom. In 2014, Dean famously cheated on Tori, and the woman he cheated with, Emily Goodhand, spilled all the details in an interview with Us Weekly. Dean later ended up going to rehab for sex addiction, and he and Tori are still married to this day.

  • 12. Jessica Simpson & Nick Lachey

    Jessica Simpson, Nick Lachey
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    After less than four years of marriage and a reality show, Newlyweds: Nick and Jessica, on MTV, this couple found themselves in the middle of an extremely public divorce. At first, Jessica Simpson and Nick Lachey separated, and then, in 2005, Jessica filed for divorce. During a 2015 interview on CNBC's Closing Bell, she revealed that her biggest financial mistake was marrying Nick -- which makes sense since she had to pay him $12 million, thanks to no prenup. 

    "The biggest money mistakes? I don't know. For some reason I thought of my first marriage!" she said, according to MSNBC.

  • 11. Johnny Depp & Amber Heard

    Johnny Depp, Amber Heard
    Splash News

    Johnny and Amber's relationship was an extremely volatile one. At the time that they split in 2016, Amber accused him of abusing her during a fight, claiming that he'd hit her in the face with a phone, and that he had emotionally and physically abused her throughout their entire marriage. In 2019, paperwork obtained by The Blast stated Johnny denied these claims, saying that it had actually been Amber who abused him. It's not clear what the truth is just yet, but either way, it's pretty obvious this was a toxic relationship.

  • 10. Justin Bieber & Selena Gomez

    Justin Bieber, Selena Gomez
    Splash News

    Justin and Selena had a turbulent, on-again, off-again relationship. From 2011 to 2018, Justin  and Selena dated, breaking up frequently -- and their relationship was constantly making headlines. And although Justin is now married to Hailey Baldwin, reports have surfaced as recently as July 2019 from Radar Online that he won't stop calling Selena.

    Will it ever end?!

  • 9. Charlie Sheen & Denise Richards

    Charlie Sheen, Denise Richards
    Splash News

    Charlie Sheen and Denise Richards' marriage seems like a scary one, especially considering what she said when she asked for a restraining order against him in 2005. According to TMZ, at the time, Denise claimed that Charlie shoved her while she was holding their daughter, Lola, and that he had told her that he was going to have her killed. Even as recently as 2015, Charlie continued to verbally abuse Denise, tweeting that she was a "heretic washed up piglet shame pile."

    But knowing Charlie's history, is any of this really surprising?

  • 8. Pamela Anderson & Tommy Lee

    Pamela Anderson, Tommy Lee
    Todd Williamson/Getty Images for PETA

    Pamela and Tommy Lee may have only been married for three years, but it involved two children, a sex tape, and plenty of headlines. Toward the end of their marriage, Tommy even spent time in jail for abusing Pamela -- six months, to be exact. It's definitely for the best that they went their separate ways.

  • 7. Ashton Kutcher & Demi Moore

    Ashton Kutcher, Demi Moore
    Splash News

    Demi Moore and Ashton Kutcher's relationship and marriage were super high profile, mainly because of their 15-year age difference. But it all came to the end in 2011, after six years of marriage, reportedly because Ashton cheated on Demi with Sara Leal, according to Us Weekly. In 2018, Ashton revealed on Dax Shepard's Armchair Expert podcast that he didn't eat for a week after their split.

    "Right after I got divorced, I went to the mountains for a week by myself," he said. "I did no food, no drink, just water and tea. I took all my computers away, my phone, my everything. I was there by myself, so there was no talking. I just had a notepad, a pen and water and tea for a week."

  • 6. Madonna & Sean Penn

    Madonna, Sean Penn
    Splash News

    During their four-year marriage, Sean was rumored to have abused Madonna. But in 2015 court documents obtained by The Hollywood Reporter, Madonna said he never hit her. Even so, things came to an end in 1989, following a 60-day jail sentence for Sean in 1987 after he was convicted of reckless driving and punching an extra on one of his movies. Their divorce was said to be amicable, but it's hard to know what really happened behind the scenes.

  • 5. Kenny Chesney & Renee Zellweger

    Renee Zellweger, Kenny Chesney
    Splash News;Splash News

    Interestingly enough, Kenny and Renee were only married for four months before they split in 2005. In a joint statement at the time of their divorce, they said "different objectives" forced them apart. But it doesn't seem like Renee looks back on this time in her life fondly. In fact, in 2006, she told British magazine Now that Kenny didn't have "acceptance of my life or my friends."

    "I made the biggest personal mistake of my life," she said at the time, according to MTV. "I felt a fool. I was looking for something else. I just needed to put acting aside. I needed to sit still and not to worry about the dresses and the hair and the travel and the interviews. I was going through huge life changes at the time. I wanted to stop and be a girl for a while. My marriage came during this time and it was desperately important to me. I don't want anyone to think I didn't take it seriously."

  • 4. Mel Gibson & Oksana Grigorieva

    Mel Gibson, Oksana Grigoriera
    Splash News

    In 2010, Oksana accused Mel of abusing her and filed for a restraining order. At the time, she said he had punched her on multiple occasions, even breaking a tooth and giving her a concussion. Later that year, tapes of Mel lashing out at Oksana hit the internet, leading him to being sentenced to three years of probation.

  • 3. Ariana Grande & Pete Davidson

    Ariana Grande, Pete Davidson
    Splash News

    The world was shocked when, just weeks after they started dating, Ariana and Pete announced their engagement, complete with a ring and matching tattoos. But it didn't last long. By October, it was over. And as Ariana told Vogue in the August 2019 issue, their whole relationship was "highly unrealistic."

    "I met Pete, and it was an amazing distraction," she said. "It was frivolous and fun and insane and highly unrealistic, and I loved him, and I didn't know him."

  • 2. Tom Cruise & Nicole Kidman

    Tom Cruise, Nicole Kidman
    Ron Galella, Ltd./Ron Galella Collection via Getty Images

    Nicole and Tom were married for 11 years, and when they divorced in 2001, Tom got custody of both of their children. Earlier this year, reports from The Daily Mail surfaced claiming that Tom was banning Nicole from their 24-year-old son Connor's wedding. Rumor has it that Tom's faith in Scientology is what made them split, but Nicole told Who magazine that she has no regrets.

    "There were times following [the divorce] when I thought, 'Wow, this is the loneliest, loneliest existence.' But with Tom, it was a fantastic decade," she told the magazine in 2012, according to E! News. "I wish all of the people that have been involved in my life well, because it's very important to me to be in a place of forgiveness and love."

  • 1. Angelina Jolie & Billy Bob Thornton

    Angelina Jolie, Billy Bob Thornton
    Splash News

    When Billy Bob and Angelina first got together in 2000, they were known for their quick, passionate love -- and the fact that they wore vials of each other's blood around their necks. But they only stayed married for three years, and in 2018, he told HFPA in Conversation podcast that they would have stayed together if what they wanted out of life wasn't so different. 

    "We just had different lifestyles," he said. "Hers is a global lifestyle and mine is an agoraphobic lifestyle. So that's really, that's the only reason we’re probably not still together, maybe. There was a different path in life we wanted to take."

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