In my undergraduate Chaucer class we've just finished our read of The Knight's Tale. We wondered if its genre (romance) actually offers a structure adequate to answering the philosophical questions Chaucer introduces into the story from Boethius. We wondered about Palamon's complaint against the cruelty of the gods, Arcite's deathbed ruminations on "What is this world?" and Emily's desire to drop out of the story completely. We wondered, in short, about fate, chance, providence, fortune, predestination, omniscience and divinity.
My brother has been wondering the same thing. Only he is a lawyer/journalist/MBA and much more clever than I am. And he is addicted to puns.
update: frater meus gets medieval: on magna carta and h. ross perot