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Twelfth Night (1969)
I've written about William Shakespeare here before, but only in a limited sense. This seems like a good spot to go in more detail.
In college, I took an acting class and I performed a scene from Hamlet. I thought I had a grasp of the meaning behind the lyricism of the words and the outdated language, but only after I read and re-read the scene a bunch of times. I think you have to see Shakespeare performed by professionals to get a real sense of what's going on and what his characters are meant to be like.
It's a stereotype that the British do him better than anyone else, but he's part of their national heritage. It kinda makes sense! His words just sound better when they come out of the mouths of Patrick Stewart or Judi Dench or Kenneth Branagh — though we Americans are no slouches when it comes to the Bard. I once saw Richard III with Denzel Washington at Shakespeare in the Park, for example, and he was riveting.
Still, when it comes to the Bard, none of these people can compare to that great, great Polish actor, Josef Tura. You've probably heard of him.
Viola, the main character, searches for her missing brother by disguising herself as a man. Why? I'm not sure. The version I watched, a UK television production from 1969 starring Joan Plowright, was fine, but it left me no clearer on this point. She didn't seem in any imminent danger as a woman, her country wasn't at war with the country she was in, and she wasn't the practical joker type. Maybe it's one of those things you have to accept as a given.
As a woman impersonating a man, Plowright doesn't bother lowering her rather high-pitched voice, but then, she is supposed to be a young man. Never mind the fact she was forty when she made this film — I certainly didn't believe she was as young as she was supposed to be — but the production made the film look like a play, so again, you gotta roll with it.
I suppose this is no sillier than A Midsummer Night's Dream or The Taming of the Shrew. I was willing to play along until the end, when Viola's masquerade is lifted and everyone somehow seemed okay with her deception. That made no sense to me...
...though it was no fault of the cast. Alec Guinness was particularly good. One forgets that before he first picked up a lightsaber, he was a really good comedic actor.
this essay from the British Library on Shakespeare and women actors.
Finally, I'm sure you'll be thrilled to know the one time I performed in drag was at summer camp a little over twenty years ago. It was talent night, and these 8-year-old girls roped me into doing a skit with them where I played a woman getting a makeover at a beauty salon. Didn't have to do much; they did all the real work. How did it feel to wear a dress? Meh. The context was more cutesy than provocative.
Other gender bending films:
Some Like it Hot
The Rocky Horror Picture Show
Hedwig and the Angry Inch
La Cage Aux Folles