The 9 Most Volatile Celebrity Relationships!

Published on June 3, 2014. Updated April 4, 2017

We can’t help but be fascinated by really tempestuous relationships, especially when the people involved are rich, talented and beautiful celebrities. Over the years, we have come across many relationships in Hollywood that are incredibly dysfunctional; however, since there are so many, it is hard to keep track of which are the most turbulent. We have created a list of the 9 most tumultuous and toxic relationships in recent history. From epic fights to public Twitter rants, these couples are, by definition, the most volatile in Hollywood. Enjoy!

9. Denise Richards and Charlie Sheen

Charlie Sheen has always had trouble getting along with women and his relationship with Denise Richards is proof of that. The “Anger Management” star allegedly threatened her life when she took their eldest daughter to get infant immunity injections and, once the divorce proceedings were underway, he would send her hateful emails. “You are a pig. A sad, jobless pig who is sad and talentless and, um, oh yeah, sad and jobless and evil and a bad mom, so go [expletive] yourself, sad, jobless pig,” Sheen wrote in an email to Richards.

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8. Sean Penn and Madonna

When Sean Penn and Madonna were married, they allegedly got into violent arguments all the time. The Oscar-winning actor was also said to be a drinker, which didn’t help matters. In 1988, Penn reportedly flew into a rage when he discovered that Madonna was having an affair with Warren Beatty. After she reportedly called the marriage off, Penn broke into her home, tied her to a chair and beat her for 9 hours. He was charged with felony domestic assault, but he ended up pleading to a misdemeanor.

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7. Tommy Lee and Pamela Anderson

Tommy Lee and Pamela Anderson had a rather tumultuous relationship. In 1998, the former Motley Crue drummer was arrested for attacking Anderson while she cuddled and breastfed their youngest son. According to the “Baywatch” star, Lee was jealous of the attention she was giving their children, which prompted him to become violent. He served four months in prison for spousal abuse; however, these two ended up reconciling in 2001 and again in 2008. Fortunately it didn’t work out in the end.

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6. Justin Bieber and Selena Gomez

Justin Bieber and Selena Gomez have been on a romantic roller coaster for a few years now. These two makeup and breakup on a regular basis and, despite all of the drama, neither one stays away for long. When they broke up in January, things became quite dramatic over text. “We r done. U need to grow the f**k up,” Gomez reportedly texted, adding, “I hope you get jail time. U deserve it at this point.” Bieber responded with, F**k YOU!!!!!” I need to grow up?! HA ok! Enjoy life with OUT ME B***H!!! F**k you. IAM DONE.”

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5. Amy Winehouse and Blake Fielder-Civil

Amy Winehouse and Blake Fielder-Civil had one of the most toxic relationships in recent history. Winehouse had been pretty straight-laced; however, that all changed when she became involved with Fielder-Civil. He admits that he introduced the Grammy-winning singer to drugs and self-harming behavior, which led to her untimely death. “I made the biggest mistake of my life by taking heroin in front of her. I introduced her to heroin, crack cocaine and self-harming. I feel more than guilty,” Fielder-Civil told News of the World in 2008.

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4. Lindsay Lohan and Samantha Ronson

Lindsay Lohan and Samantha Ronson had an incredibly rocky on-off relationship. According to Ronson’s mother Ann Dexter-Jones, the “Mean Girls” star threw an epic temper tantrum while her daughter was DJing the opening party in Dubai, which made her realize that the relationship was anything but healthy. “It seemed she was upset that people, including Samantha, were not paying her enough attention. To my mind, it was classic psychotic behavior,” she said.

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3. Charlie Sheen & Brooke Mueller

Charlie Sheen’s relationship with Brooke Mueller wasn’t that different from the relationship he had with Denise Richards. In 2009, the “Anger Management” star spent Christmas in jail after he got into an argument with Mueller that turned violent. Sheen was arrested for domestic violence, second degree assault, felony menacing and misdemeanor criminal mischief. According to police reports, this wasn’t the first time he had been violent towards Mueller.

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2. Chris Brown and Rihanna

Chris Brown has a history of being violent towards Rihanna. Before 2009, when he was convicted of felony assault for beating her unconscious, he had already physically assaulted her. Despite this, Rihanna cannot seem to stay away, even when he has a girlfriend. When Brown moved on to Karrueche Tran, Rihanna was quick to get in there and break them up; however, nothing ever lasts between her and Brown.

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1. Mel Gibson and Oksana Grigorieva

Mel Gibson and Oksana Grigorieva had an extraordinarily volatile relationship. In 2010, she was granted a restraining order against him after he physically assaulted her, breaking some of her teeth. During their custody battle, audio recordings of the “Braveheart” star disparaging Grigorieva surfaced and it wasn’t pretty. “I’ll put you in a f **kin rose garden you c**t! You understand that? Because I’m capable of it. You understand that?” Gibson ranted on the recordings.

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