69. Sasha Grey
Age (circa 2009): 21
Occupation: Adult Video Star
Sure Sasha Grey was 11 when the Aughts began (think about that, pervert), but her work in the past two years in the adult film industry has done more for men's imaginations than most who have come before her. She might not be as smart as she and the rest of the world might hope, but she can act like she's enjoying it somethin' fierce.
Transcending the adult industry by starring in The Roots' "Birthday Girl" video and Steven Soderberg's The Girlfriend Experience.