Charlie Sheen isn’t shy about his sex life. Rumored to have slept with over 5,000 women, Sheen openly flaunts his conquests as proof of his immense, insurmountable awesomeness. Surely the man has been with more women than he can remember by name, face, or decade in which he had sex with them, but here’s a short list of some of his more notable romantic endeavors.
Sean Penn’s longtime lover was one of Charlie Sheen’s earliest documented romantic endeavors. He and Wright got together when they were both up-and-coming teenage actors in the early 1980s.
Sheen was involved with Winona Ryder for a short time in 1986, probably after appearing in teen-oriented comedy flick Lucas together.
Cathy St. George
Socialite Tracy Richman was a fixture in the Hollywood party scene for years, and in Sheen’s bed for a few months in the early 1990s.
Kelly Preston became the focus of what was arguably Sheen’s first major public relations fiasco when he accidentally shot her in the arm with a gun in 1990, leading Preston to break off their engagement. Now she’s married to John Travolta, who has yet to shoot her with anything.
In her day, Dominique Simone was the most sought-after African American porn actress in the industry. Naturally, this meant Sheen had to have her. And he did.
Sheen saw something special in porn actress Ginger Lynn. The couple dated for two years, from 1990 to 1992, and she stayed by his side when he entered drug rehab during that period.
It’s well known by now that Sheen loves himself a good porn star. Heather Hunter was a big name in the industry at one time, and another notch on Sheen’s bedpost.
Donna Peele and Sheen were married in 1995 and divorced a year later.
Ashland stands out among Sheen’s former lovers as one of the few to accuse him of assault. In 1996, Ashland sued Sheen for allegedly pulling her hair, slamming her on the ground and knocking her unconscious. She required seven stitches in her lip after the incident. Sheen pleaded no contest and agreed to settle the case.
Sheen married Denise Richards in 2002. They stayed together for three years and had two kids before Richards filed for divorce in 2005, citing Sheen’s drug and alcohol abuse as a detriment to the relationship and claiming that Sheen had threatened her with violence.
Sheen’s third marriage was to Brooke Mueller in 2008. A real estate investor and total smokeshow, Mueller was a change of pace for Sheen, who had primarily involved himself with celebrities and porn stars before then. The two are still legally married, though they’ve been separated since 2009 when Mueller accused Sheen of assaulting her.
Kacey Jordan was one of the many porn stars who partied with Sheen during his now-infamous 36-hour sex-and-drugs bender earlier this year.
Porn star Melanie Rios was also present for Sheen’s monster bender.
Another of Sheen’s recent porn star conquests, GiGi rivera was actually with Sheen when the paramedics arrived following his post-bender crash-and-burn in January.
When rumors started swirling that Sheen had locked a chick in the closet before trashing an expensive New York hotel room in October 2010, people wondered aloud who it had been. Turns out it was porn star Capri Anderson, who had apparently locked herself in the bathroom to escape Sheen’s destructive tirade.
Natalie Kenly and Bree Olsen
Natalie Kenly and Bree Olsen get grouped together because, as it turns out, Sheen is dating them both concurrently. He refers to them as his "goddesses" and they all share a bed together, and, as Olson puts it, when it comes to the trio’s sex life “We do whatever Charlie wants us to do.” Damn, Charlie. Just damn.
That’s not all.
Not by a long shot. Here are a few more of Sheen’s rumored flings:
This, gentlemen, is what winning looks like.