Cass Sunstein's essay 'On Bob Dylan' describes Dylan's 'dishabituating' style -- a constant refusal to conform to expectation and a penchant for reinventing his musical and lyrical identity. In this paper, I extend Sunstein's observations through a large-scale computational analysis of Dylan's lyrics from 1962 to 2012. Using o3-mini-high (a large language model), I extract concept-to-concept relationships from the lyrics and construct directed knowledge graphs that capture Dylan's thematic structure. I then quantify shifts in sentiment, metaphorical expression, thematic diversity, and network complexity over time. The results indicate that Dylan's lyrics increasingly rely on metaphor, display an evolving sentiment profile, and exhibit heightened dishabituation -- measured here as a growing variance in the network centrality of key concepts. I also find that references to movement, protest, and mythic imagery fluctuate in ways that align with well-known phases of Dylan's career, reflecting the dynamic and unpredictable quality of his art. These findings not only deepen our empirical understanding of Sunstein's thesis but also introduce a novel computational method for analyzing an artist's evolution-offering broader applicability to the study of cultural and creative change.