So. "Measure for Measure" is actually really interesting! I've never personally read it before, but I know that it is actually my high school English teacher's favorite Shakespeare play as well. This is a fascinating connection between two teachers that actually might have a supernatural origin, but that's beside the point.
I've heard of it called 'a problem play' before, as well, when said English teacher was trying to describe the plot of it before. And, to be honest, I never really grasped what that meant. It was funny, like a comedy, but things weren't so black and white and twin-switchery and such. But that's about it.
Now, though, I think I'm beginning to understand the concept of a problem play, which is nice. It's funny enough, but with wayyy darker tones than most comedies usually have. I also am much more emotionally invested in these characters than I usually get with a Shakespeare comedy. For instance, in "A Midsummer's Night Dream", I really don't care what happens to the characters, as I know it's going to turn out pretty okay at the end. But with a play like "Measure for Measure", I'm genuinely concerned with what's going to happen with Isabelle, and her idiot brother.
This play hurts in a way that a usual 'comedy' would not. I don't want Isabelle to compromise her ideals and what she believes is moral and right in the eyes of God, but I also don't want idiotic Claudio to die for having sex with the woman he loves. So I'm conflicted, and I can feel the problem here.
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I felt the exact same way while reading. It's like the play always kept me on my toes and I never knew what was going to happen to whom. I knew what I wanted to happen, but Shakespeare has a way of coming up with things I never would have thought about. I also found myself sympathizing with Isabelle and Claudio, hoping things would end well for both of them.
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