4. Charlie Sheen – 5,000
If you think having sex with around 5,000 women, a lot of them prostitutes, is “winning,” then you andCharlie Sheen would get along just fine. Sheen, as we all know, was a former movie star, turned TV star, who then turned into, well, Charlie Sheen.
Sheen has allegedly had sex with Brittany Ashland, Brooke Mueller, Denise Richards, Heather Hunter, Sherilyn Fenn, Robin Wright, Winona Ryder, Heidi Fleiss, and probably someone you know personally.
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