I will say this for the Canterbury Tales, it makes Shakespeare much easier.
After finishing Chaucer's tales, I didn't want to drop back into easy modern prose, so decided to read a Shakespeare play that was new to me. Reading the Canterbury Tales first definitely helps. While Shakespeare is modern English, he uses some of the same sentence structures and vocabulary that seem so odd to us now. As a result, I fairly tore through Twelfth Night.
I have to admit that I came away from the play without a strong feeling about it one way or the other. I would guess, though, that it's much more enjoyable watching it rather than reading it; the characters would be much more humorous and modern interpretations could have fun with it.
The play itself is full of very confused people, who seem to be so bewildered by disguises and social shifts that they'll cling to any conclusion. It reminds me most of a game in which the pieces are interchangeable, though some of them have to be matched up in the end. The fun is to see how many different permutations they can run through first.
I have to wonder how much this play is about Shakespeare mocking courtly love and its forms, and how much he was just having a good time.
