It has always been used as a form of comedy, and therefore it is engrained in our society that it is funny. The mindset immediately took to film, with some of the first films including cross-dressing for comic relief. Charlie Chaplin was at the forefront of using this for comedy with The Masquerader (1914) where his character is fired from a studio, so he dresses as a woman to return, and A Woman (1915) with Charlie Chaplin portraying a woman so he could spend more time with his girl friend. The trend continued for countless films, but I will mention two in particular, Tootsie and Sorority Boys. Tootsie is a classic movie, and widely regarded as having feminist undertones. In Tootsie, Hoffman plays an actor, Michael Dorsey, who is having trouble getting work in Hollywood. He dresses up as a woman to get a role in a soap-opera, and after receiving said part, he must continue to live his life as a woman to the public. Dorothy is brave, independent, and