After starring in a series of hit films in the latter half of the 1980s— Platoon, Wall Street, Young Guns, and Major League— Charlie Sheen’s acting star was on the rise. However, his personal life was in shambles—in early 1990, Sheen accidentally shot actress Kelly Preston, his then-fiancée, in the arm. “One night we thought we had prowlers; the burglar alarm went off, and I put my .22 in the pocket of my pants,” Sheen later claimed. “It turned out to be nothing. I forgot about the gun, left my pants in the bathroom, and the next evening, Kelly was moving my clothes when the pistol went off. A bullet hit the toilet, and shrapnel hit Kelly's ankle and wrist.'' Nonetheless, Preston split—running into the arms of her current husband John Travolta. She reportedly went on to sell the 2.5 carat engagement ring Sheen had given her, but was allegedly kind enough to split the money with him.
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After his relationship with the comparatively clean-cut Preston fizzled, Sheen began dating adult-film actress Ginger Lynn in 1990, setting off a long line of XXX-rated relationships. Sheen and Lynn dated for two years, including a dual drug-rehab stint. The relationship garnered a great deal of media attention, with Sheen taking a palpable PR hit for dating a porn star at the height of his Hollywood fame. In 1991, Lynn was convicted of falsifying a tax return, landing her in jail for four and a half months. Sheen and his father Martin reportedly wrote letters to the court on her behalf. Later that year, Lynn checked herself into rehab for a cocaine addiction and though their relationship ended in 1992, she still has fond memories of Sheen. “The first and last time I have ever been in love,” Lynn said of the actor. "He was the first man ever to break my heart… I don’t think I would ever date anyone with that high a profile again. We broke up publicly long before we broke up privately. It was basically managers, agents, and attorneys and his mom. She didn’t care for me.”
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After cutting ties with Allen, Sheen briefly moved on to another adult-film star in 1994. He began seeing Heather Hunter—at the height of her pornographic fame—after meeting her at a party. A decade later, Hunter appeared with Ginger Lynn in Hustler’s 2004 film Can You Be a Pornstar? 3 & 4. “He was a gentleman,” Hunter recently told Hollywood Life of Sheen. “I think with life, people see the good side and the bad side of certain people. I never saw the [bad side] of him. I guess it was a fortunate thing.” Hunter explained she “didn’t see that crazy side,” and described the Two and a Half Men star as “really nice, concerned and compassionate.”
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After being outed as one of the many celebrity clients that frequented Hollywood madam Heidi Fleiss’ brothels in her 1995 court case, Sheen married Elite model Donna Peele in a 1995 ceremony at the Saddleback Ranch in Malibu. "I'll just say Charlie is totally in love with Donna," Sheen’s bodyguard, Chuck Zito, said at the time. "I wish them all the luck in the world." But unfortunately, their love was fleeting and Sheen separated from Peele after slightly more than five months of marriage. Following the split, he was rumored to be heavily pursuing porn star Jenna Jameson, who recently offered advice for the women in Sheen’s unofficial adult-star alliance. “Run! Run! Screaming!” Jameson told Fox News with a laugh. “I think I might have been one of the very first girls in the [porn] ring. He stalked me, and it wasn't good.”
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In 1996, another porn star became the object of Sheen’s affection. He briefly dated then-25-year-old Brittany Ashland, but she didn’t have the same kind words that fellow adult-film actresses Lynn or Hunter did. On Feb. 6, 1997, Ashland filed a lawsuit against Sheen claiming that he grabbed her by the hair and slammed her onto the marble floor of his California home, knocking her unconscious and splitting her lip open, requiring several stitches on Dec. 20, 1996. She also alleged that Sheen threatened to kill her if she said a word about the incident. “Rarely do celebrity men take responsibility for their actors,” Ashland’s lawyer, Gloria Allred, told People magazine. But the actor eventually pleaded no contest to misdemeanor battery charges and was sentenced to a one-year suspended prison term and two years probation and ordered to pay $2,800, perform 300 hours of community service, and attend eight counseling sessions. At his sentencing, Sheen reportedly told the judge, "I feel this is very fair, and I'm grateful… you will not see me back in this courtroom," according to the Los Angeles Times. Though her case was settled, Ashland recently served as a character witness against Sheen when he was charged with assaulting his most recent ex-wife Brooke Mueller on Christmas Day in 2009.
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After meeting in 2000 on the set of the box-office dud Good Advice, Sheen married former Bond girl Denise Richards on June 15, 2002. The couple had two daughters together, but while Richards was pregnant with their second, she filed to divorce Sheen in March 2005, accusing him of being unstable, violent, addicted to gambling and prostitutes, and a frequent visitor of pornographic websites featuring young men and women who appeared to be underage. Their divorce was made official on Nov. 30, 2006, and, following a bitter, lengthy custody dispute over their children, the two have since made peace. In fact, according to The New York Daily News, Richards ate dinner with Sheen and his “date,” porn star Capri Anderson prior to his notorious meltdown at the Plaza Hotel in October 2010 and she also accompanied him to the hospital. “All she wants is for him to be healthy,” an insider recently told People of Richards' feelings for Sheen.
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In March 2005, while Richards was busy separating from Sheen, porn star and escort Chloe Jones sold a story to the National Enquirer claiming that Sheen paid her $15,000 for oral sex in January 2005. And Richards used the claim during her divorce proceedings in an effort to gain spousal support. When Jones died later that year, suffering from liver failure as a result of alcohol and prescription-drug abuse, Richards claimed in court that when she questioned him about whether he had a hand in the porn star’s death, he replied, “No comment.”
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In April 2006, non-porn star Ursula Auburn—who says she had several romantic encounters with Sheen between 1992 and 1998—filed a lawsuit against him claiming that the "wacky neighbor and female stalker Rose” (pictured here) on Sheen’s hit CBS TV sitcom, Two and a Half Men, was based on her. Auburn alleged that the way Rose dressed and talked resembled her, and that several of the plotlines were reminiscent of things that happened between herself and Sheen in real life. The disgruntled woman sought more than $1 million in damages and Sheen eventually settled the case on March 14, 2007, though details were not disclosed.
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In 2008, things seemed to finally be looking up for the beleaguered sitcom star. Sheen married his third wife, real-estate investor Brooke Mueller on May 30 in an intimate ceremony. “They’re well-matched and incredibly happy,” a friend of the couple told People. Nearly a year later, on March 14, 2009, Mueller gave birth to the couple’s twin sons, Bob and Max. Then, however, the two were involved in another in a long line of holiday weekend scandals. Sheen was arrested on charges of domestic violence, including second-degree assault and menacing in an incident that allegedly lead to him holding a knife to Mueller’s throat. On August 2, 2010, Sheen pleaded guilty to misdemeanor assault and was sentenced to 30 days in rehab, 30 days of probation, and 36 hours of anger-management classes. Meanwhile, Sheen and Mueller haven’t been seen together in public since the altercation and Sheen filed for his third divorce on Nov. 1, 2010.
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Of all Charlie Sheen’s scandals, his meltdown at the Plaza may be the biggest. On Oct. 26, 2010, after a night of reported partying, police busted into Sheen’s room at the famous Manhattan hotel to find the place a mess and the actor naked, high, and ranting. Sheen was carted off to the hospital and, to make matters worse, 23-year-old porn star/escort Capri Anderson was found naked, locked in the bathroom. Anderson made the publicity rounds, appearing on Good Morning America claiming that she was paid $3,500 to accompany Sheen to dinner, and later that night, when things got romantic, he went ballistic. The actor countersued for extortion, claiming that Anderson was a prostitute who is just after his money. A series of flirty text messages following the Plaza Hotel fiasco indicated that the Two and a Half Men star offered her $20,000 to set things straight, and that the two were on fairly amicable terms, despite her allegations.
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Just one month ago, on Jan. 10, Sheen was at it again. The Two and a Half Men star hooked up with multiple porn stars— including Jesse James’ tattooed mistress Michelle “Bombshell” McGee and 24-year-old porn star Bree Olson— during a wild booze-and-drug fueled orgy, according to TMZ. The three were allegedly inside the $40,000-per-night Hugh Hefner Sky Villa inside the Fantasy Tower at the Palms Casino Resort in Las Vegas. Following the incident, Olson’s friend told Page Six that she believed she had a shot at romance with Sheen. “She doesn't understand why he doesn't get serious with his girls,” the source said.
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The latest in the timeline of Sheen’s troubles took place on Jan. 27 when paramedics took him to Cedars-Sinai Medical Center for “severe abdominal pains.” Of course, this came following an alleged 36-hour drug binge with a gaggle of porn stars at his palatial California mansion. One of the actresses along for the ride, Kacey Jordan, said that Sheen smoked cocaine out of a pipe all night while watching porn. She also claimed that he ordered in a briefcase full of cocaine and wanted her to babysit his daughters when he moves into a separate mansion populated with porn stars in what he allegedly referred to as a "porn family." At one point, Sheen reportedly cut a $30,000 check made out to cash and gifted it to one of the porn stars. Despite the crazy soiree, it was later reported that Sheen had to be hospitalized for aggravating a preexisting hernia by laughing too hard at the TV.
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