Edited by Lester Brathwaite on
While there are certainly more instances of men dressed as or portraying women in film than the alternative, those depictions are not always positive. Either played for laughs or for fear, Hollywood has a rich history of sexual exploitation, but the following films offer more than just a boy in a dress.
Ed Wood in Glen or Glenda (1953)
Originally intended to be a film about transsexual pioneer Christine Jorgensen, noted transvestite/worst movie director of all time Ed Wood instead made a piece about cross-dressing, advocating tolerance.