Who do you think is the greatest Shakespearean villain of all time?
Also, I don't know if you're familiar with it, but I recently was acquainted with Cymbeline. Online it's called a tragedy, but my Pelican Shakespeare calls it a comedy...(and it reads as a comedy).
Anyway, it's now one of my favorites and IMO highly underrated. It's got a little blood :)
Hard to pick one, but Iago's got to be in any list.
I agree about Cymbaline -- it's complicated and witty, and like his other late plays, it straddles comedy, tragedy, and romance.
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