In this chapter, I explore Dylan’s self-referential use of the ballad form: he innovates in terms of content (crafting quasi-allegorical figures that subvert the referential nature of classic ballads) and in terms of form (instead of linear narratives, we encounter condensed or fragmented tales). I read the condensed outlaw ballad “John Wesley Harding” through the lens offered by Derrida’s essay on Kafka “Before the Law.” Drawing together Kafka’s concern with subversive parables and Derrida’s investigation into the law of genre and how it illuminates the working of the law in general, what seems a simple throwback to outlaw balladry becomes an investigation into how texts depend on and question the limits of the law. A central argument in this chapter, based on archival research, is that Bob Dylan similarly explored the dynamic interpretive possibilities of proverbs (both biblical and literary) in terms of proverbial form. Rather than using this form of writing to encode or dispense wisdom, he uses the proverbial form in these ballads to question how wisdom is received, interpreted and circulated. This is a deconstructive play I align with the satirical work of William Blake, especially his “Proverbs of Hell.”