While it may have deeper implications today than it did decades ago, men dressing like women is one of the oldest forms of comedy. It is at the heart of one of the best feature comedies ever made, Some Like It Hot, as well as several other classic comedy films, Tootsie, Mrs. Doubtfire and The Birdcage, and it has had a presence on TV, most notably with the 1980 series Bosom Buddies starring Tom Hanks, and Saturday Night Live where male cast members regularly impersonate female celebrities. And then there is the British school of comedy with Monty Python and Benny Hill. ABC’s president Paul Lee brought up his heritage when explaining his decision to pick up Work It to critics at the summer TCA press tour. “I’m a Brit, it is in my contract that I have to do one cross-dressing show a year,” he said. “I was brought up on Monty Python. What can I do?” As a fellow European who also grew up with Monty Python and Benny Hill, I can actually relate to that...."I can see the Brit excuse, but it's really awful, if you're going to indulge in argument by listmaking like that, to leave out the most prominent — in more ways than one — cross-dresser in the history of television, the man who was called Mr. Television, Milton Berle.
Here's a great clip of Berle in drag — in a guest spot on Lucille Ball's show. (If you've only got 2 seconds to spare, click here.)
By the way, what a concentration of comic acting in that 5-minute clip, from everybody involved, including Desi Arnaz, who, if he showed up on TV today, would probably elicit criticism from some dignity-protecting group that doesn't care whether or not comedy has room to breathe.