#57: Heidi Fleiss’s Prostitution Ring Busted

“You’re not paying a hooker to have sex,” Two and a Half Men star Charlie Sheen once famously said. “You’re paying her to leave afterwards.” Sheen should know. At 1995 the trial of Hollywood Madam Heidi Fleiss, it emerged that the son of movie icon Martin Sheen had spent some $50,000 on prostitutes in just over a year.

Sheen’s was the most public face in Fleiss’s very public bust. During the 1990s she ran a prostitution ring whose client list included movie and political types who, if we mentioned them, would sue us into the poorhouse. (Hint: Not Larry Craig.) It’s a bitch-eat-bitch world in Hollywood: Fleiss’ boyfriend turned her in (he was launching his own call-girl ring), while Sheen was offered up as a B-list patsy for the prosecution.

In 1997, Fleiss was sentenced to 37 months in jail for charges related to her prostitution business. Upon her release, she embarked on a (failed) attempt to start a brothel for women in Nevada. But the scandal did wonders for Sheen, who’s since developed into one of the highest paid actors on TV, earning $350,000 per Half Men episode. — Charles Bottomley