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21. Heidi Fleiss
Heidi Fleiss appeared to be the typical Los Angeles woman: attractive, ambitious, and brimming with life. She was a prominent figure in the media during the ’90s and appeared on a variety of shows. What some people did not know is what Heidi Fleiss did during her spare time.
Fleiss managed to build a lucrative empire that required her to do just one thing: provide some of the most influential people of all time with favorable call girls, at a sweet price of $1500 per night. She very quickly earned the name Hollywood Madam. Her kingdom crumbled after a police sting, which ultimately led to Fleiss being charged with multiple felonies. She served a little over three years in prison.
