Charlie Sheen. Crazy as heck, with a history of failed relationships, drug rehabilitation, and the strangest catchphrases, such as “tiger-blood” and “#winning.” He is one of the creepiest and saddest actors that we have seen in a long time. And while he started out as a great actor with tons of potential, now he is just drowning ever deeper into the pit of despair. From his HIV diagnosis to his tumultuous romances and flings around the adult film circuit, to his multiple divorces and lawsuits, is there any hope left for poor Charlie Sheen?


We aren’t sure, but what we do have for you is a list of The 20 Sexiest Women Charlie Sheen Has Been With. While Charlie gets compared to Donald Trump, we are going to take a step back from him and focus on the many women that he has been with. Charlie may be a lost cause now, but back in his heyday, he was quite the stud. He was able to get many girls and he even married some of them. Donna Peele, Denise Richards, Brooke Mueller, and his ex-fiancee Brett Rossi; these are just some of the ladies who have been romantically linked to the wild and crazy actor. You also better believe he’s had his fair share of adult stars, with over 10 of them appearing on this list!

So sit back and take a look at Charlie Sheen’s intimate inventory of porn stars, reality TV stars, and B-list models. He sure knows how to pick ‘em, huh? In all seriousness though, these women are attractive and we hope that they recover from their time with Mr. Sheen.

Brett Rossi

 Brett Rossi almost became another wife of Charlie Sheen. The couple were engaged, but Brett reportedly called it off after realizing just how drunk with rage Charlie always was. Stating that the romance was toxic and super violent, she walked away from him. Good on ya, girl. She also filed a lawsuit against Charlie for assault and battery. Brett had formerly worked in adult entertainment (no surprise there) and said that Charlie was ready to settle the lawsuit for $1,000,000, but then he backed out. Citing love, then fear, Brett (who is about 3 decades Charlie’s junior) described their scary relationship and said she even feared for her life.
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