Top 10 Cross-Dressing Movie Performances

Dustin Hoffman in Tootsie

Everett

When asked about Tootsie, a film whose most basic premise slightly resembles that of his all-time classic Some Like It Hot, director Billy Wilder said, “Tootsie was very good, but they tried to make it a little too serious with that element of actors looking for parts and not getting them, or whatever.” But what Mr. Wilder, blessed be his name, didn’t seem to understand is that the “element of actors looking for parts and not getting them” was the movie. It’s about show biz, about difficult actors, and about the lengths they must go to in order to practice their profession. When actor Michael Dorsey (Dustin Hoffman) fails to close on yet another audition, he decides to dress up as a female character of his invention — Dorothy Michaels. She immediately gets a soap opera role and the requisite drama ensues. In his Oscar-nominated role, Hoffman completely inhabits Dorothy — he becomes Dorothy to the point where we sometimes forget that this is a movie about a man playing a man playing a woman. All we see is her.

Next: Tim Curry in The Rocky Horror Picture Show