As demonstrated so well by Jack Lemmon and Tony Curtis in Some Like it Hot, men in drag will always be a great source of comedy in American film. The tradition of men dressing as woman goes back to the plays of Shakespeare being used as a comic device as early as the 16th century. The sexual confusion that comes from the characters in these films has been revisited several times in other American comedies with varying levels of success.
Here are two of my personal favorites.
Tootsie, starring Dustin Hoffman and directed by the recently departed Sydney Pollack, came out in 1982 and became a massive critical and financial success. The multilayered love triangles that are explored in this film are very reminiscent to the plot of Some Like It Hot. In the film Hoffman plays an out of work actor who can only get work if he auditions for a female role on a hit soap opera. This plot device is very similar to the situation of Curtis and Lemmon in Some Like It Hot minus the gangster violence.
Another great example of cross-dressing explored in comedy is The Bird Cage. A remake of an earlier French film called La Cage Aux Folles. Here Robin Williams and Nathan Lane a committed gay couple who own a drag bar must play it straight when their sons fiancés family comes to meet their new in-laws. Obviously the fiancés father is an extremely conservative politician running for reelection. The snappy dialogue and situational comedy is hilarious every time I see it.
If you haven’t seen these movies you should because they stand the test of time as classics just like Some Like It Hot.
Here is a list of Cross Dressing on Film
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