Famous for: The most infamous Hollywood Madame with little black book that could made grown men weep. Literally. After all her little black book was a Who is Who in Hollywood.
What went wrong? Heidi Fleiss had a rather successful operation going that was until she was arrested and charged for operating a prostitution ring, tax evasion and pandering. She served 21 months in prison while none of her customers were charged. She was involved with Tom Sizemore and she accused him of domestic violence and other violent behavior, one of which includes making obscene phone calls.
One would think in her line of work she had heard it all, but there you go. She has a boutique in Hollywood called Hollywood Madame (very original!) and plans to built a brothel in the state of Nevada called Heidi Fleiss’ Stud Farm. This year she was arrested for DUI and illegal possession of prescription drugs.