To this day, Shakespeare’s Twelfth Night remains one of his most widely read, performed and adored comedies. Wonder if it has something to do with the cross-dressing.

Seriously. There is a lot of cross-dressing in this one. Yes, true, it’s only one character who does the dressing up, but it’s a pretty central point of focus, and when you also consider that the women were all played by men in the first place in Shakespeare’s time, you have a truly confusing (albeit entertaining) scenario. The issue stands out even more because plays about cross-dressing were simply not done back then. (Again - interesting, since half the actors on stage in any play during that time were cross-dressing.)

It was feared by certain members of the community that the very act of dressing in the clothing of the opposite gender would turn women into hermaphrodites. (There’s a vocab word that may pop up on your PSAT.) Yeah, we’re sure there were a lot of actual case studies of that happening for them to draw from. Nevertheless, the subject matter and treatment of it were frowned upon and heavily criticized, which probably thrilled Shakespeare, as he was such a controversy enthusiast.

SAT Prep (37751)Of course, today we all know the real truth, and that is that cross-dressing is just plain funny. No offense to the thousands of people who dress that way for reals - we’re just referring to the comedic use of transvestism as applied in popular culture. Monty Python and Benny Hill figured it out, and in more recent years there have been such films as The Hot Chick, White Chicks and She’s the Man (instant classics all of them) that have employed cross-dressing for humorous purposes. (She’s the Man, by the way, was actually a modern retelling of - you guessed it - Twelfth Night.) You practically need to be an AP Calculus stud just to keep track of how many cross-dressing references there are in contemporary television and film. (Okay, so counting doesn’t really entail having to know any calculus - you’ll please forgive us for our hyperbole.)

But it must have been even funnier in Shakespeare’s time, because there was that added ‘should we be laughing at this?’ vibe going on. Ah yes - he was the South Park of his generation. The playwright was no stranger to venturing into taboo or unexplored territory (that’s one of the reasons he’s the best!). Many of his female characters (such as Lady Macbeth and Kate in The Taming of the Shrew) were intelligent and strong-minded - something else that wasn’t really being done. Romeo and Juliet was the first love story to be referred to as a tragedy, and his portrayal of certain historical figures came under fire as well.

So what have we learned? Well, that controversy is funny, obviously! Ever heard Robert Downey Jr.’s well-known speech in Tropic Thunder, or seen Borat or Knocked Up? If so, you’ll know what we mean.