RuPaul: Fairest of Them All (2001)

This documentary explores the life of RuPaul Charles from his humble beginnings to his transformation by dint of personality and ambition from a 6-foot-4 gay black man into a towering blond multitalented supermodel.

His creation, RuPaul, became the first cross-dressing act to ever reach the pop charts with the 1993 hit "Supermodel." By thrusting drag into the American mainstream, RuPaul had a great impact on the acceptance of gays by the general public.