This paper explores the ways in which the Barbershop Harmony Society’s flexible and contested constructions of musical content relate to the community’s originary myths, to its ongoing negotiations of social and organizational values, and to specific musical practices. Drawing on documentary evidence, interviews, and participant observation, I argue that barbershop’s rather fitful and intermittent espousal of a form of Werktreue ideal can best be understood in the context of the idiom’s characteristic approaches to music making. The theoretical fissures that riddle the Barbershop Harmony Society’s definitive discourses, meanwhile, reflect the tensions between different sets of musical and social values simultaneously in play among Society members. Recent debates within the Barbershop Harmony Society about membership levels, breadth of appeal, and repertoire consequently emerge as a tension between the ideals of Preservation and Encouragement that it was founded to promote.