This dissertation approaches the Canterbury Tales through the lens of humor theory, responding to a much-noted gap in existing scholarship by focusing primarily on the structures and mechanisms of humor in the text. In attending to humor as part of Chaucer's response to cultural anxieties, I illustrate the ways in which Chaucer makes space for a wide range of readers by carefully situating his jokes to create "in-groups" across significant cultural divisions. I argue that humor in the Canterbury Tales diffuses anxieties about cultural change by creating a flexible imagined space in which canny readers or listeners may laugh at the same joke from multiple perspectives. In doing so, Chaucer's humor allows audience members to experience and embrace feelings of superiority, power, and control over targeted aspects of larger issues.