This chapter surveys the various contexts through which my study will analyze the songs on Bob Dylan’s album John Wesley Harding. The chapter argues that the uses to which Franz Kafka put the form of the proverb and the parable are useful paradigms for understanding Dylan’s radically condensed and textually enigmatic songs on this album. The chapter also argues that Dylan’s return to a folk music in these songs is, in fact, a deconstruction of certain values of the folk revival (authenticity being key among them). As well, the chapter explores the urban uprisings of the summer of 1967—when Dylan composed the songs for John Wesley Harding—in order to read the album as a response to the historical and political pressures those cataclysmic events placed upon national narratives of belonging and progress. Additionally, concepts relevant to the exploration of those historical contexts—specifically the law and justice—are analyzed through a Derridean lens to further question, in the spirit of the songs, how these terms functioned in the political discourse of the day. In that way, I argue Dylan’s album, rather than being a retreat from politics, is deeply engaged with its political moment.