5. TOOTSIE (1982)

Cross-dressing has always been a popular theme in pop culture. Consider Monty Python or The Kids in the Hall, which constantly involved men dressing as women. Film is no exception, with successful films like Some Like It Hot and Mrs. Doubtfire creating comedy with cross-dressing themes. Tootsie, however, is often put into another category: a movie that's funny, but not because it has a man dressing up as a woman.

Let's take a step back and see what the movie's about: Michael Dorsey (Dustin Hoffman) is an out-of-work actor who needs money. But he's so hated in New York, that he finds it impossible to get a job. His solution: dress up as a woman, and create a whole new personality named Dorothy Michaels. He quickly gets a job on a General Hospital-esque soap opera as the Hospital Administrator, and things are just ducky. Unfortunately, he falls in love with a woman who plays a nurse on the show (Jessica Lange), and she thinks he's a woman. And we're not even 20 minutes into the movie. . .

Tootsie is known for several things, but is probably most famous for Dustin Hoffman's convincing portrayal of a woman. Dorothy is not a caricature or a joke; she's a legitimately real creation. No one would look at her and think it's a man in drag. Compare this to other films, where the man in drag always seems to make a hideously ugly woman and you think: any fool would know that's a man! (Exception: The Crying Game . . . oy!)

Michael encounters several levels of conflict. Is Dorothy a feminist icon, and if so, how can he get out of pretending to be her for his entire life without making a mockery of women? How can he get the nurse to love him when he knows that she'll never forgive him for fooling her? And what about the nurse's dad (Charles Durning), who has fallen in love with him? And what about Michael's current neurotic quasi-girlfriend (Teri Garr), who thinks that he's seeing another woman because he saw one go into his apartment (of course, it was Michael as Dorothy)? Whaddamess. . .

The other thing that makes Tootsie such a success is its screenplay. It doesn't play for slapstick, and it doesn't assume that everybody is a moron. It also contains funny scenes outside of the primary story (such as Dustin's argument with his agent about whether an actor portraying a tomato should walk or not).

So in a nutshell, Tootsie is not really about cross-dressing. That's just the vehicle for analysis. Tootsie is really about how people pretend to be something other than what they are, and how managing all of those facades just causes problems. This brings us back to our original statement: the cross-dressing is not what makes Tootsie work (although it is funny). It's the believability of Dorothy as her own character that makes it great.

Notes:

  • Made almost $180 million

  • Nominated for 10 Academy Awards (including Best Picture, Best Actor, and two Best Supporting Actress nominations)

  • Won 1 Academy Award: Best Supporting Actress for Jessica Lange

  • Won 3 Golden Globe Awards: Best Picture, Actor, and Supporting Actress

  • Placed #62 on the American Film Institute's "100 Greatest Movies" List