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Heidi Fleiss was a Hollywood madam who supplied the rich and famous with companionship for the night thanks to her ring of good-looking women.

Fleiss herself was said to have dated Charlie in 1988. When Fleiss was arrested for tax evasion and pandering in 1995, Sheen even testified against her and admitted to spending over ,000 on the women she supplied.

This was before Winona hit her big break in the film Heathers.

Once Winona hit it big, her and Charlie ended their relationship amicably.

It is slightly sad that we remember him for his escapades and not his career, but he did that to himself.

begin Hard to imagine but Sean Penn’s ex-wife, Robin Wright, also known to us as Buttercup, dated Charlie Sheen from 1981 to 1982.

The women on this list were all proven to be with Charlie, most of whom were linked to him around the same time!

His father, Martin Sheen, sure wouldn’t be proud to know his son was such a party boy.

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Robin’s other famous roles were in the film Forrest Gump, Nine Lives, Everest, and Wonder Woman.

Some were easy to find, especially the famous ones, while others were practically impossible to find since they have gone underground after their Sheen relationship.

Charlie has been in the press in recent years for everything except his acting.

Ross sued Sheen for million and won as she accused him of being violent towards her, exposed her to the HIV he was hiding for years, and had made her get an abortion. It seems as though she has diverted all of her energy towards fighting Sheen and getting the most out of her relationship with him.

She went so far as to changing her name to Scottine Sheen prior to even marrying. George was Playmate of the Month in August of 1982. While her time with Sheen was short, they did attend Hollywood events together, as we can see in the following photo.


  1. Nov 17, 2015. Two former girlfriends of Charlie Sheen, who on Tuesday admitted that he is HIV positive, have denied the actor's claim that he told them, as six women. “I was his girlfriend. I lived with him. We were together. We had sex almost every day for a year.” Bree Olson, Charlie Sheen and Natalie Kenly in 2011.

  2. Jun 2, 2017. Charlie Sheen and his new girlfriend, Jools. Danimal/Splash News. Now a year later, Sheen posed for pictures with Jools for the paparrazi and chatted with photographers as soon as she emerged from their car. "This is my girlfriend, that's Jools," he said. "No one's got a photo of us yet." Sheen and his the.

  3. Jul 18, 2016. Jess Impiazzi gushes about her romance with HIV-positive Charlie Sheen for the first time. British glamour model Jess Impiazzi has told of the abuse she's received for dating HIV-positive actor Charlie Sheen. 'The people who go out of their way to say horrible stuff, they are the ones with the problem.

  4. Jun 23, 2017. An ex-girlfriend of Charlie Sheen has filed a lawsuit accusing him of exposing her to HIV, and then dissuading her from taking antiretroviral drugs. He also referred to other women he had slept with and who were threatening him with legal action over HIV exposure as “f—ing n—–s” who had committed.

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