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1. Winona Ryder

Winona Ryder Source:Getty

Long before Winona Ryder was a household Hollywood name and light-years before she was convicted of shoplifting, Winona Ryder dated Charlie Sheen in 1988 while they were filming the movie “Lucas.”

2. Charlie Sheen & Kelly Preston

Charlie Sheen Source:Getty

Charlie was briefly engaged to John Travolta’s now-wife/actress Kelly Preston in the early ’90s. After “accidentally” shooting her in the arm, the two actors subsequently broke up.

3. Charlie Sheen & Cathy St. George

Charlie Sheen Source:Getty

After his breakup with Kelly Preston, Charlie Sheen dated adult star Cathy St. George. She was Playmate of the Month in August 1982 and kept very close ties to the Playboy Mansion.

4. Charlie Sheen & Ginger Lynn

Charlie Sheen & Ginger Lynn Source:Getty

Charlie’s love for porn stars didn’t start in the 2000s. After his breakup with Kelly, Charlie dated porn star Ginger Lynn.

5. Heather Hunter

Charlie Sheen Source:Getty

After a brief relationship with Ginger Lynn, Charlie moved on to the most famous Black porn star in the ’90s – Heather Hunter.

6. Charlie Sheen & Donna Peele

Charlie Sheen Source:Getty

Donna Peele was Charlie Sheen’s first wife, whom he married in 1995. The marriage didn’t last very long. After Charlie was outed by famous Hollywood madame Heidi Fleiss for being her most famous client, Donna filed for divorce.

7. Heidi Fleiss

Charlie Sheen Source:Getty

Charlie Sheen didn’t exactly date Hollywood madame Heidi Fleiss, but he was outed by the female pimp during her trial for being one of her high-profile clients.

8. Brittany Ashland

Brittany Ashland Source:Getty

In the mid-90s, Charlie Sheen dated model/actress Brittany Ashland. The relationship ended in court after Brittany accused Charlie of allegedly beating her. With Gloria Allred by her side, Charlie eventually pleaded no contest and was given a suspended jail sentence.

9. Charlie Sheen & Denise Richards

Charlie Sheen Source:Getty

Charlie married actress Denise Richards in 2000. After a tumultuous marriage where domestic violence and drug-use reigned supreme, Denise filed for divorce from Charlie in 2005.

10. Charlie Sheen & Brooke Mueller

Charlie Sheen Source:Getty

Charlie Sheen married his third wife Brooke Mueller in 2008. The couple made headlines when Brooke filed a restraining order against Charlie accusing him of domestic violence. Just a few years later, the two were divorced.

11. Charlie Sheen & Capri Anderson

Charlie Sheen Source:Getty

Capri Anderson is the woman Charlie Sheen was found drunk, naked, and locked in a closet with. The then-aspiring porn star/high-paid escort said Charlie appeared to be attempting suicide via extreme cocaine use. Allegedly, Charlie was snorting lines of cocaine every few minutes for days.

12. Kacey Jordan

Charlie Sheen Source:Getty

Kacey Jordan is the porn star Charlie allegedly paid $30,000 to spend two days with in 2011.

13. Charlie Sheen, Bree Olsen, and Natalie Kenly (The Goddesses)

Charlie Sheen Source:Getty

Remember Charlie Sheen’s epic meltdown when “winning” and “tiger blood” ruled his life? Well, former porn star Bree Olsen and Natalie Kenly were right by his side. Both women lived with Charlie for over a year during his crash. Bree, who was actually Charlie’s live-in girlfriend, maintains the actor never told her about his positive HIV status.

14. Charlie Sheen & Brett Rossi

Charlie Sheen Source:Getty

Charlie became engaged to model/actress Brett Rossi in 2014. Like most of Charlie’s relationships, this one was also dysfunctional. Brett accused Charlie of domestic violence during a series of tweets. She also said Charlie didn’t tell her about his HIV status until four months into their courtship.

15. Mia Isabella

Mia Isabella Source:Getty

Transgender porn star Mia alleges she was in a brief relationship with Charlie Sheen and cited that he, along with rapper Tyga, were “very influential” in legitimizing her adult career in Hollywood.

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