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When Geoffrey Chaucer died in 1400, he was more famous for having been the Clerk of the King's Works than for writing The Canterbury Tales. Oh, what a difference 600 years makes! This is the grand-daddy of all Chaucer works and a fascinating look into life in the fourteenth century.
True Chaucer buffs say that Troilus and Criseyde is actually his best work. Chaucer had a habit of starting poems and not finishing them. (If you think The Canterbury Tales is long, consider that Chaucer finished only 24 tales out of the 100 that he'd planned.) Troilus and Criseyde is the only poem that he actually completed. It's a Middle English take on the classic Greek love story.
Chaucer poses a challenge to his biographers. There are significant legal and royal records that tell us about the dry details of his life, but nothing to reveal who he was as a person. This critical biography does its best to analyze Chaucer's character through his works and historical record.
Famed literary critic G.K. Chesterton wrote a series of biographies about the Great Writers. This is his take on Chaucer. It's a succinct, elegant guide to Chaucer's life and significance.
The great English poet T.S. Eliot was fascinated by the 1170 murder of Thomas Becket, the archbishop of Canterbury whose shrine Chaucer's pilgrims are en route to visit. He penned this play about the murder of Becket, who is now worshipped as a saint by Catholics and Anglicans.
Medievalist Ian Mortimer's book is a light-hearted guide to all things medieval. If you suddenly learned that you would be traveling alongside Chaucer's pilgrims on the road to Canterbury, this would be your guide to acting like a local. Mortimer explains customs, cuisine, and even bathroom habits of medieval Englishmen.