Against the darkest period of his life, Chaucer undertook his greatest literary accomplishment, The Canterbury Tales. He worked on this project for 14 years, from 1387 until the end of his life in 1400. According to his plan, there were to have been 120 tales, with each pilgrim telling four stories: two on the way to Canterbury and two on the way back. He did not complete the full plan for his book, however; the pilgrims never reach Canterbury, and there is no return journey from Canterbury. Some of the pilgrims do not even tell stories. Twenty-eight pilgrims are introduced in the Prologue, not counting the host and the narrator. Two out of 24 extant tales are unfinished (the Cook’s and Squire’s).

The Canterbury Tales are the most celebrated work of Chaucer, which tagged him as a modern poet and the father of poetry. The work is unique in its individualizing of the narrator and the depiction of the contemporary social scene. He brings together the representatives of every class in the England of his day.

The Canterbury Tales begins as a group of thirty pilgrims gathers at the Tabard Inn in Southwark, near London, to embark on a pilgrimage to the shrine of St. Thomas at Canterbury. The shrine in the Canterbury Cathedral was one of the most popular sites in the fourteenth century England. Archbishop Thomas a Becket was murdered there in 1170. The blood from his wounds had been preserved and soon revealed miraculous powers for healing the sick. The journey from Southwark to Canterbury in Kent could take two days on horseback, though it usually took three days.

Chaucer sharply characterizes his pilgrims through the sketches of the narrator in the General Prologue and the vivid relationships between the characters, as well as the tales they tell. The tales are fascinating in themselves, but are even more fascinating in what they tell us about the tellers. Chaucer the pilgrim, Chaucer the narrator, and Chaucer the man hovers over the narrative he created. His tone is jaunty, and he is interested in the complexity of the human condition, which he views with an irony that is, as G. K. Chesterton said, “sometimes so large that it is too large to be seen.”

By using the frame of the pilgrimage, Chaucer was able to bring together and represent people from many walks of life: knight, prioress, monk, merchant, men of law, scholarly clerks, miller, reeve, pardoner, wife of Bath, and many others. In addition to this diversity, the setting of a storytelling competition allowed him to present different literary genres: romance, fabliau, saint’s life, allegorical tale, beast fable, medieval sermon. Chaucer had already used the framing tale technique in his Legend of Good Women, and the poet John Gower applied to his Confessio Amantis (1385). The most famous antecedent of the framed tales is Boccaccio’s The Decameron, an Italian work (1351-53). Chaucer, of course, wrote in Middle English, and his works were intended to be read aloud to an audience.

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