1995

Dubbed the "Hollywood Madam" for running a high-priced prostitution ring serving Tinseltown's rich and famous (The most high-profile man identified as a client was actor Charlie Sheen). Fleiss was convicted on federal charges of conspiracy, tax evasion and money laundering.

After the prostitution charges were dropped she received a 37 month sentence of which she served 20 months before being released to a halfway house to finish the remainder.