100. Ashley Dupré
Age (circa 2009): 24
Once a good girl's gone bad, she's gone forever. Need proof? Look no further than Ashley Dupré. She ran away from her privileged Jersey suburb to NYC at 17 and was working as an escort by 19. A few years later, she found herself at the center of the prostitution scandal that brought down New York governor Eliot Spitzer. Even crazier, Girls Gone Wild footage of an underage Dupré surfaced after the story broke. Some may call her trashy, but with an hourly rate of $5,500, we prefer to call her economically sound.
Being crowned "the most famous hooker in America" by The Village Voice after she was outed as Elliot Spitzer's side piece. 'Round here we call that a FAIL.