Tootsie is about a man who transforms into an older woman in order to remain employed as a New York actor. In this interview he describes how depressing it was to actually live out certain aspects of being a woman.
As I get older (and by implication, less attractive) it's interesting to watch myself become more and more invisible to other people. Sometimes invisibility is a huge benefit, but it's also a little bit shocking. It's comforting to know that someone, a man, sympathizes with that challenge.