The Stunningly Awful Love Life Of Charlie Sheen

The following article contains multiple references to domestic abuse allegations.

When Jon Bon Jovi said "You Give Love a Bad Name," he could very well have been singing about Charlie Sheen. For a brief period in the late '80s and early '90s, the actor attracted a huge fan base with his boyish charm. But it's been a hot minute since he starred in a movie or popular TV show. Indeed, these days, the "Two and a Half Men" alum is more famous for his controversial personal life than his acting career. When it comes to Charlie's love life failures, some might argue that he's second to none.

The son of acclaimed veteran actor and passionate activist Martin Sheen, it's difficult to fathom what went wrong with Charlie. When the father-and-son duo starred alongside each other in 1987 classic "Wall Street," the younger Sheen depicted a man who gets caught up in greed and excess, but through his humble father's sagacity, he learns the difference between right and wrong. If only the actor could have gleaned this insight in his own life. 

Since his most critically acclaimed role, Charlie has found himself in one endless downward spiral. In addition to his bizarre Howard Beale-esque rants and adherence to outlandish conspiracy theories, he has been accused of all manner of heinous crimes in his romantic relationships, almost to the point of jaw-dropping disbelief. Yep, Charlie had a hot shot at love time and time again, only to ruin his chances of having a fulfilling and long-lasting relationship. He's not #winning at love: Get ready for the stunningly awful love life of Charlie Sheen.

Back in 1989, a fresh-faced Charlie Sheen was engaged to fellow actor Kelly Preston, who later had a seemingly unconventional marriage to John Travolta. The former relationship, however, would spur one of Sheen's most legendary myths: Rumor has long had it that Sheen allegedly shot Preston, thereby ending their courtship, per Newsweek. As far as absurd Charlie Sheen stories go, this one might seem pretty believable — but turns out we've had it all wrong.

According to reports, Preston was shot in the arm and had to be taken to hospital, where she received stitches. But Sheen claimed that the gun accidentally went off. While on tour in 2011, he gave an expletive-laden speech (via E! News) to a crowd of fans and finally explained what actually happened that fateful day (according to him, at least). "I was downstairs early in the morning making coffee and I thought she was still asleep upstairs," he recalled. "And I heard a f***ing gunshot go off. I thought, 'She did it. ... She killed herself and they're going to f***ing blame me.'" The actor said that he rushed to the stairs, only to find Preston covered in blood. "I thought, that's pretty f***ing hot," he, um, quipped. Sheen then explained that Preston accidentally shot herself when she took his pants off the bathroom scale; unbeknownst to her, there was a gun in the pocket.

Speaking to TMZ that year, Preston insisted that Sheen did not shoot her and the whole debacle was an accident blown out of proportion.

Charlie Sheen's first wife was model Donna Peele, whom he wed in 1995. Per The Spokesman-Review, Sheen met his love on a modeling shoot. "Just when I thought I was the luckiest guy alive, I just got a lot luckier," he gushed at the time. "She's my best friend, and we've both found our soul mates." But their marriage was blighted by salacious tabloid stories. As Sky News noted, Sheen was embroiled in a huge scandal involving self-styled Hollywood madam Heidi Fleiss, who claimed that the actor had dozens of sexual encounters thanks to her services. Accordingly, his relationship with Peele soon disintegrated.

That year, Sheen testified at Fleiss' trial. Per the Los Angeles Times, the "Hot Shots!" star told the jury that Fleiss arranged for him to meet at least 27 sex workers, spending a whopping $50,000 on various sexual encounters. Discussing the actor's apparently avaricious sexual proclivities in 2018, Fleiss claimed to The Hollywood Reporter that Sheen heavily downplayed the number of women he procured from her — and the total sum of the escapades allegedly amounted to a small fortune. "On the stand he said a much lower amount than he actually spent with me," she claimed. "He probably spent closer to $300,000 or $400,000 on girls. He said something like $60,000." 

This scandal would be one of Sheen's earliest, but it certainly wasn't his last. In time, the star developed a reputation that has surpassed even our wildest expectations.

Is Charlie Sheen a sex god? He (and his ex) seem to think so. Adult performer Ginger Lynn, who dated the actor in the early '90s, has detailed the supposed origin story of his legendary bedroom prowess. "I helped Charlie become the amazing lover he is today," Lynn told The Sun in 2011 (via Digital Spy). "He was good — but I helped him to give back that little bit more." Lynn claimed that Sheen was initially a selfish lover, but her tutoring enabled him to learn how to satisfy (innumerable) women.

In an interview with the Los Angeles Times from around this time, Lynn further alleged to have seen an aspect of Sheen that is seldom discussed. She painted the actor as a misunderstood soul with a deeply sensitive side. "There's a side of him that I don't think many people hear about," she explained. "Especially because right now, everyone's focusing on the negative. I have the soft, the considerate, the sensitive, the warm, the scared, the encouraging sides."

Indeed, unlike many of his subsequent relationships, Sheen and Lynn did appear to share a deep bond. Radar published a letter that Sheen wrote on behalf of his lady love in 1991, when Lynn was facing prosecution for tax evasion. "Ginger is, in my opinion, one of the finest people I've ever known," he told the judge in part. Despite Sheen's efforts, Lynn ultimately did jail time.

By the late '90s, Charlie Sheen became romantically involved with adult performer Brittany Ashland. Sadly, their relationship was anything but rosy. Shortly into their romance, Ashland alleged that Sheen had subjected her to domestic violence.

In 1997, Sheen was charged with misdemeanor battery after Ashland detailed the brutal assault allegedly inflicted upon her late the previous year, per the Los Angeles Times. According to CBS News, Ashland was reportedly thrown to the floor by her hair and needed stitches in her lip following the alleged attack. She also claimed that she was warned not to go to the police, out of fear that Sheen would kill her. Although the actor initially maintained his innocence, with his reps calling Ashland's claims "a cheesy attempt at extortion," he eventually pleaded no contest to battery. 

Subsequently, he was handed two years' probation on the condition that he receive counseling and perform community service. According to CNN, Ashland's lawyer, Gloria Allred, also facilitated a settlement between the two, though the terms remain private. A probation violation in 1998 marked a particularly low point in Sheen's personal life, as his father and young daughter, both appearing visibly distressed, sat in the courtroom as testimony was read, per UPI. Things remained acrimonious between Sheen and Ashland; in 2010, she stated that she wanted to testify against her ex when he was again accused of domestic abuse, this time by his then-wife, Brooke Mueller, per Digital Spy.

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

In 2002, Charlie Sheen married for the second time, to Bond girl Denise Richards. It appeared that the twosome were madly in love, with Sheen getting his new bride's name tattooed on his wrist, per People. The actor claimed to have been a changed man, telling the outlet, "There's not hope for much when you're that deep. [Denise] has taught me more about myself than anybody I've ever been close to. I just feel so supported all the time." The couple welcomed two children together, Sam and Lola, born in 2004 and 2005, respectively.

Although things seemed to be looking up for the troubled star, Richards began to notice that her husband was allegedly engaging in some particularly troubling behavior, and she subsequently filed for divorce in 2006. In court documents obtained by TMZ, Richards alleged that she caught her husband watching apparent child abuse videos of "very young girls, who looked underage to me, with pigtails" and "gay pornography also involving very young men who also did not look like adults." Accordingly, Richards was granted a restraining order from her ex, and his visitation rights were also restricted. 

Denying his ex's accusations, Sheen told TMZ that Richards had allegedly set out "a most obvious immature and transparent smear campaign designed to hurt, embarrass and ultimately extort me." In 2015, he dubbed Richards as the "worst mom alive" in an admittedly nasty Father's Day Twitter rant that has since been deleted, per Us Weekly. Yikes.

If you or someone you know may be the victim of child abuse, please contact the Childhelp National Child Abuse Hotline at 1-800-4-A-Child (1-800-422-4453) or contact their live chat services.

The old adage says that third time's a charm, but for Charlie Sheen, his relationship with wife No. 3 ended as catastrophically as one would expect from the self-proclaimed tiger blood king. Sheen met actor Brooke Mueller against the backdrop of his acrimonious split from Denise Richards in 2006, per People. At the time, Mueller told the outlet that she was trying not to be fazed by the bad blood between her beau and his ex-wife. "We just focus on our love," she said in part. The couple tied the knot in 2008, and Sheen expanded his brood when he and Mueller welcomed twin sons the following year, as Us Weekly reported.

Unfortunately, but perhaps not unsurprisingly for bad boy Sheen, this would prove to be yet another failed marriage. On Christmas morning 2009 — the couple's first festive season with their sons — Sheen allegedly tried to kill Mueller, according to The Guardian. She claimed that he threatened her while holding a knife to her throat. According to her police report, Sheen warned, "You better be in fear. If you tell anyone I'll kill you. ... I have ex-police I can hire who know how to get the job done and they won't leave any trace." 

Accordingly, he was arrested on suspicion of domestic violence and spent Christmas Day in jail, per Today. Appearing in court in 2010, Sheen eventually pleaded guilty, as reported by the Independent. He was sentenced to probation and ordered to attend anger management classes and rehab.

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

Charlie Sheen was long known for his worrisome behavior, but his outlandish antics arguably reached their pinnacle in 2010. It was revealed that he took adult performer Capri Anderson to a New York City hotel, where he reportedly began behaving erratically, trashing the room in a violent outburst. According to sources cited by TMZ, Anderson reportedly claimed that Sheen had been holding her against her will; afraid for her safety, she allegedly locked herself in the bathroom. 

But Sheen, who was taken to a hospital following the alleged coke-fueled rampage, insisted that the story was being blown out of proportion. "Oh my man, I'm fine. ... I know what went down and that's where it will stay ... under wraps," he told Radar. The actor's publicist further claimed that the outburst was caused by a negative reaction to his medication. Sheen later filed extortion charges against Anderson, asserting that she fabricated claims of him choking her (he also accused her of stealing his swanky $165,000 watch), per Radar. However, he dropped the case in 2011, as the Independent noted. 

In a bizarre twist, Radar reported that the duo had reconciled in 2013, with Anderson apparently moving into Sheen's home. "Charlie's been partying almost harder than ever. It's one of the only things him and Capri have in common!" an insider claimed. "Charlie and Capri pretty much just act like none of that craziness from the past ever happened. It's the weirdest thing." Then again, is anything weird in the world of Good Time Charlie?

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

Much has been made of Charlie Sheen and his so-called goddesses. Following his divorce from Brooke Mueller in 2011, he formed a throuple with adult performer Rachel Oberlin (best known by her stage name Bree Olson) and graphic designer Natalie Kenly, both of whom were in their 20s. Sheen discussed his ménage à trois with ABC News, declaring that he was living his best life. "It's perfect. It's awesome. ... These are my girlfriends. These are the women that I love that have completed the three parts of my heart," he enthused. Meanwhile, Oberlin revealed that she was eager to marry Sheen, who hinted at being open to the idea of a polyamorous marriage.

But not everyone was thrilled with this arrangement. Oberlin's mom, Marie, told People that she was concerned for her daughter, having discovered that she was romantically involved with the older actor after turning on the TV. "I tried calling Rachel right after that. ... But there was no answer," she explained. "I wonder what he promised her. I just don't want to see her hurt."

All good things must come to an end, however, and for Sheen, the end was nigh. A few months later, he revealed that Oberlin dumped him in a text message, per the Los Angeles Times. Ouch. In 2015, she slammed him for allegedly exposing her to HIV without disclosing his diagnosis (thankfully, she didn't test positive). However, Kenly defended him, telling ET that Sheen wasn't HIV positive when the trio were together.

Following his disastrous relationships with his first three wives, Charlie Sheen moved onto Scottine Ross (also known as Brett Rossi) and swiftly popped the question. But as with all things Sheen-related, this engagement was anything but straightforward. As Radar reported, Ross was still married to her husband, Jonathan, when Sheen proposed in 2014. Like many of Sheen's lovers, Ross is an adult performer, but in a surprising move, he swooped to his fiancée's defense when outlets reduced her to her sex work. "It's absolutely making Charlie crazy that the media keeps referring to Brett as a porn star. ... She recently graduated from nursing school," an insider said.

Despite a promising start, the couple called it quits later that same year. Sheen told the Los Angeles Times that although he and Ross had a fabulous time together, including traveling the world, he called off their engagement so he could focus on his kids.

In 2015, Ross accused Sheen of physical and emotional abuse and filed a lawsuit against him for allegedly exposing her to HIV. Speaking with People, she claimed that the actor beat and isolated her, and also made her quit her dream of becoming a nurse. "I'm scared he wants to kill me," she revealed. Per the Los Angeles Times, she was granted a restraining order against her ex after he apparently threatened to have her kicked in the head. Sheen denied all accusations against him, though the lawsuit was apparently eventually settled, per the Daily Mail.

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

When it comes to messy relationships, Charlie Sheen is winning. Throw Tyga and Kylie Jenner into the mix, and this tale becomes an abyss worthy of a Jules Verne-level deep dive.

Sheen began a close relationship with adult performer Mia Isabella circa 2012. According to a video posted to Isabella's YouTube channel in 2014, she was introduced to Sheen after he told one of her pals that he was eager to meet her. The two embarked on a relationship, though Isabella denied that they were anything but friends. She was also linked to Tyga around this time (however, he denied being romantically involved with her). As reported by InTouch in 2015 (via the Mirror), Kylie Jenner apparently became fearful that she may have been exposed to HIV due to her then-boyfriend supposedly sharing an ex with Sheen. "As soon as Kylie's mom, Kris [Jenner], found out about Tyga's connection to the same ... woman that Charlie was involved with, she went ballistic," a source claimed. "For obvious reasons, Kris insisted that Kylie get to the bottom of this potentially life-threatening mess." Considering that Isabella insisted that she and Sheen were just friends, it seems highly unlikely that Tyga was exposed to HIV through Sheen.

In a rare case of an alleged Sheen ex who parted with him on amicable terms, Isabella has had nothing but praise for the controversial star. "My memories of him reflect a warrior and super brave person. ... I have nothing but admiration for his friendship," she told ET.

Having sex with someone while knowingly infected with HIV and failing to disclose it is illegal in many states. Yet, Charlie Sheen's the first to admit he did just that with some previous partners. In 2015, he went public with his HIV diagnosis. Appearing on Today, he conceded that he did sleep with people after discovering he was HIV-positive in 2011, but claimed that transmitting the virus to any of his partners was "impossible."

Speaking at a 2016 event in London (via Radar), Sheen confessed that he didn't tell a number of his lovers about his HIV status. "The only times I didn't tell them, was because the last 25 times they used it against me, and used my medical condition for their own folly, and financial gain," he said, though he claimed he didn't have unprotected sex with anyone. "Here's the great news ... no one has been infected by me. No one," Sheen added. "They claim, the sorrow and the pity, or whatever. But that's on them, I know the truth."

Understandably, his admission angered many of his exes. In addition to Scottine Ross' previously mentioned lawsuit, another of Sheen's exes accused him of exposing her to HIV. Per Variety, the anonymous woman filed a lawsuit against the actor in 2017, alleging that Sheen not only lied that he didn't have HIV or any STDs, but told her not to take antiretroviral drugs when he eventually disclosed his HIV status. Per TMZ, the lawsuit was settled in August 2022 for $120,000.