In this essay, the author analyzes Bob Dylan's contentious mid-60s break with the folk movement, exploring ways in which it may have been telegraphed by his lyrics, while also acknowledging the pitfalls of seeking psychological or biographical insights into artists via their work, generally and particularly with regard to Dylan. From there, the author explores the fallout of Dylan's pivot from overtly political work, and the larger debate over what roles politics and activism should play in art and literature. Finally, the author offers two key ways in which this exploration of Dylan could be relevant to analysts.