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Troilus and Cressida
The Oxford Companion to Shakespeare mentions that early 19th Century critics were "baffled" by this play. I have some sympathy with them; I don't really know what Bill was trying to do with this one. No contemporary writer worth the name would plot the final two acts this way, for a start. Now plotting was never Bill's strongest suit but we aren't talking about one of his daft comedies where you can ignore plot development in exchange for extreme verbal and physical comedy down in the woods tonight and go home chuckling at what you've seen and heard and not really caring about the absurdity of it all. Nor is this Romeo and Juliet 2.0, despite the set up in the first three acts where we start with a lot of wit and word play and silliness but get progressively more serious as time goes on, ending up with a full-on Tragic denouement and a bold statement about the destructive nature of feuding and partisan violence within respectable society that is alarmingly relevant 400 years later. Here, if there is a Tragic figure at all it is Hector, sadly too naively trusting in others' honour because his own is impeccable, rather than Troilus or Cressida, let alone both. And the play, despite having two endings, never really resolves the issue of the Troilus-Cressida-Diomedes love triangle at all. It's a mess.
Apparently more recent criticism has focused on Shakespeare's treatment of sexuality in the play but I don't really find the idea that people can be fickle and inconstant and driven by other people's looks all that profound or interesting, though I find it believable that Bill might have been aiming at a discussion of it.
So what I'm left with is a play that starts humourous then becomes amusingly chaotic and diverting in the final act (alarums and excursions abound) but stops rather than really concludes and suffers horribly in comparison with the Iliad's treatment of all the characters they have in common - a comparison that, at least while reading off the page, is unavoidable to anyone who has previously encountered Achilles' rage as described by Homer.
And on we go to Sir Thomas More, a play for which Shakespeare wrote probably only one or two scenes.