Tootsie 1982

What do you get when you cross a hopelessly straight starving actor with a dynamite red sequined dress? You get America's hottest new actress.

Directed by Sydney Pollack

When struggling, out of work actor Michael Dorsey secretly adopts a female alter ego—Dorothy Michaels—in order to land a part in a daytime drama, he unwittingly becomes a feminist icon and ends up in a romantic pickle.