Charlie Sheen: A Timeline of Bad Behaviour

Actor Charlie Sheen has a long history of violence against women, with sexual assaults, battery and threats against women spanning over two decades. 

January 1990: While in their home, Sheen reportedly accidentally shot fiancée Kelly Preston in the arm. The relationship ended shortly after. In 2011, Sheen claimed she accidentally shot herself, using the story for a comedy routine:

"I was downstairs early in the morning making coffee and I thought she was still asleep upstairs," he said, regaling the crowd. "And I heard a f--king gunshot go off. I thought, 'She did it, she finally f--king did it. She killed herself and they're going to f--king blame me.'" So I abandoned the coffee, because a gunshot in the morning will wake you up better than a nice cup of coffee," he said, drawing increasing laughs from the crowd.

"I come around the corner and there's naked Kelly Preston at the top of the stairs, holding her wrist, staring at me, covered in blood…and I thought, that's pretty f--king hot," he explained, before quickly adding, "I didn't. I didn't." After tending to Preston, laying her down, grabbing towels and bandages and managing to stop the bleeding, he got around to asking her what happened. As you would.

"She explained to me when she lifted my pants off the scale in the bathroom…the tiny revolver I used to carry…it fell out of the back jeans pocket and hit the floor and shot a bullet right between her legs," he explained amid much interjecting from his onstage cohort. "So she got hit with shrapnel from the toilet bowl."

September 1990Sheen completed drug rehab a month after checking himself in.

October 1994: Sheen was sued by a young UCLA student who claimed he repeatedly struck her in the face and head after she refused to have sex with him. 

July 1995: Sheen testified in the tax evasion trial of Hollywood madam Heidi Fleiss, admitting he spent almost $53,000 on the prostituted women she sold. 

December 1996: Sheen was arrested for allegedly beating his girlfriend Brittany Ashland, who was also a porn performer. Ms Ashland claimed he grabbed her by the hair and slammed her head into the marble floor of his home, threatening to kill her if she told anyone. 

June 1997: Sheen plead no contest to the charges in relation to his assault of Brittany Ashland. He was sentenced to a one-year suspended prison term and two years of probation. 

May 1998: Sheen was hospitalised after a cocaine overdose. His father, Martin Sheen, turned him over to the authorities for violating his probation. Sheen later checked himself into rehab.

March 2005: Denise Richards, Sheen's second wife, filed for divorce while pregnant with the couples' second child. Richards alleged Sheen had a problem with drugs and alcohol. 

March 2005: Porn performer and escort Chloe Jones told the National Enquirer Sheen was one of her clients, and had paid her $15,000 for oral sex. Sheen's agent disputed the claim. 

April 2006: Denise Richards, Sheen's second wife, applied for a restraining order. In her statement to the court, she detailed a long history of drug use, gambling, paying for sex, abusive behaviour and threats, including threats to kill their dogs. Richards expressed her concerns about Sheen's pornography use, which included boys and girls who appeared to be underage, including girls with braces, pigtails and without pubic hair performing sex acts. Richards recalled an incident at her house on the 30th December 2005 where he pushed her over and threatened to kill her in front of their children: 

'Respondent then started to approach me. I was still holding Lola. I put my right hand up to block him and to shield myself and Lola. The Respondent pushed me, shoving me with his two hands between my shoulders. I was forced backwards and tripped over one of the children’s toys and fell on the floor with Lola. Sam was screaming the entire time and crying. Lola was also crying. When I was laying on the floor, the Respondent then pointed his finger at me and screamed,”I hope you f..king die, bitch.” I took both girls, sat on the couch and tried to calm them down. The Respondent turned away and as he was walking out the front door, said to me that he was going to have me killed. He said,”you are f..king with the wrong guy.'

In a conversation on April 9th, 2006, shortly before Richards obtained the restraining order, Sheen continued to make threats:

'He told me that “I will never get to court because I will be f...king dead!” He told me to enjoy my parents “while they are still around”. I took this to mean that he was not only going to do me harm but also do harm to my parents. In this conversation, I also brought up an old prostitute/porn star who he saw by the name of Chloe Jones. I saw on the news that she had died from undetermined causes. When I asked him if he had anything to do with her death, he said that he had “no comment”. He repeated “no comment” again when I asked him again.'

March 2008: Jason Itzler claimed he sent Ashley Dupre and another girl to have a threesome with Sheen for $20,000. Sheen's reps denied the report. 

December 2009: Sheen was arrested on domestic violence charges after an alleged altercation with his third wife Brooke Mueller, the mother of his twins, who claimed he held a knife to her throat. 

February 2010: Sheen was charged with felony menacing and misdemeanour third degree assault and criminal mischief in connection with the December arrest. He plead not guilty the following month, but eventually plead guilty and was sentenced to 30 days in rehab, 30 days probation and 36 hours of anger management.

February 2010: Sheen announced he was voluntarily checking himself into rehab. 

October 2010: Sheen was reportedly removed from The Plaza Hotel in New York after causing a disturbance and allegedly doing $7,000 worth of damage to the room. 

November 2010: Sheen was sued by Capri Anderson, a pornography performer who was with him at The Plaza, alleging he choked her and threatened to kill her. Sheen countersued Anderson, accusing her of extortion.

March 2011: Sheen's estranged third wife Brooke Mueller obtained an emergency restraining order after Sheen allegedly threatened to cut off her head, put it in a box and send it to her mother. 

October 2012: A man filed a police report after Sheen allegedly threatened to shoot him to death.

November 2013: Sheen sent an abusive tweet to his ex-wife Brooke Mueller, inviting her to fellate a hand grenade.

October 2014: Sheen was sued for assault and sexual battery by a dental technician after allegedly grabbing her breasts and punching her during a dental visit. 

June 2015: Sheen sent an abusive tweet to his ex-wife and mother of two of his children Denise Richards, calling her a "heretic washed up piglet shame pile". 

December 2015: Sheen's ex-fiancée Scottine Ross sued him for assault, battery and false imprisonment. She alleged he put an unloaded gun to her head and repeatedly pulled the trigger. 

April 2016: Sheen's ex-fiancée Scottine Ross obtained a restraining order against Sheen after a recording believed to be Sheen's voice said he would rather pay someone $20,000 to kick her in the head than settle her law suit.

June 2017: Sheen was sued by an ex-girlfriend for knowingly exposing her to HIV. Sheen knew of his HIV positive status in 2011, and had sex with her in 2015. She allegedly asked him upfront if he had any sexually transmitted infections and he said he was "fine" but told her later he was HIV positive. 


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