This one's going out to Erin Riley tonite.
The most remarkable analogies I found between Chaucer and hip-hop were not only historical, however; they were also reflected explicitly in the organizational structure of The Canterbury Tales. The text consists of a collection of stories that Chaucer wrote over the course of about fifteen years towards the end of his life. Some of the Tales were apparently composed before he began the compilation, while others were obviously tailor-made for the project. To bring all of these different stories together into one, Chaucer creates a fictional company of pilgrims riding on horseback from London to Canterbury, who all decide to play a game to help pass the time along the way: a storytelling contest. Each tale represents an entry in the contest by one of the pilgrims, and Chaucer ascribes certain personality traits to each of them, which are then reflected in the tale. What begins on the surface as a religious pilgrimage soon takes a profane turn when the stories become a vehicle for challenges and insults aimed at the other pilgrims. Chaucer employs the competition as a unifying principle, and also as a device to expose social tensions among the pilgrims, while showcasing their different storytelling techniques and levels of ability.
The clearest analogy for this storytelling contest model in hip-hop culture is the phenomenon of the freestyle battle, a live performance event that underlies the majority of recorded rap lyrics either in style or content. By definition, a freestyle is a rap that is unwritten and unrehearsed, composed by the rapper in the moment of performance, with rhymes that are improvised on beat and, when required, on topic. A freestyle battle is when two or more rappers compete in this way head to head, using punch lines, boasts, and insults to out-rhyme and outwit their opponents. The two terms aren’t interchangeable though, since written rhymes are sometimes used in battles, and freestyles are often simple demonstrations of ability rather than direct competitions. Freestyle and battling perform the same function in hip-hop culture as Chaucer’s storytelling competition does in The Canterbury Tales, dramatizing social tensions among rappers and showcasing different techniques and levels of ability. These systems were developed in response to the particular conditions of hip-hop’s genesis.