28. Capri Anderson
Cheater: Charlie Sheen
Date Of Affair: 10/26/2010
There's an old saying that goes, "It's all fun and games until somebody gets hurt." Well, that could very well be applied to the disastrous evening in October of last year when adult actress Capri Anderson was paid $3,500 to go to dinner with crazy-ass Charlie Sheen who proceeded to drink excessively and partake in other party favors until he was reportedly almost comatose. Yet he was not wasted enough to stop from allegedly hurling slurs, getting naked in the restaurant bathroom and then going back to the The Plaza hotel to get naked again while throwing a lamp and choking the porn starlet with the piercing light blue eyes, who had to hide in the bathroom for safety.
Charlie ended up in the hospital that night after the cops showed up. Capri (real name Christina Walsh) filed a lawsuit and Charlie countersued and the allegations piled up on both sides. Meanwhile, Sheen was still waiting to have his divorce with third wife Brooke Mueller finalized. Well, at least Chuck didn't cheat on her with the sexy Capri that fateful night in NYC.