It wasn't the world's oldest profession that made Heidi Fleiss a household name, but rather the world's second oldest profession. Back in 1987, the "Hollywood Madam" was convicted in connection with her high class prostitution ring (oxymoron?) and tax evasion charges. Heidi was sentenced to three years in prison, but her famous customers -- Charlie Sheen among them -- weren't punished at all. It's hard out there for a pimp(ette)!
Yet, if anyone knows how to take hookers and make, uh, hookerade, it's a business maven like the Madam. She's opened at least two stores, hocked a sex tips DVD, made many TV guest appearances, and wrote an "Ask Heidi" column for Maxim. With the rights to her life story selling for $5 million, a 1995 documentary and a 2004 made-for-TV movie, things nearly turned around for Fleiss -- aside from a 2003 domestic abuse case against ex-boyfriend actor Tom Sizemore and a drug-related arrest last year. But, we hear she's opening a legal brothel in Nevada soon. Congrats, Heidi -- that's a tabloid dream come true!