This thesis will argue that Bob Dylan’s art is one of renewal and recycling, one in which the very concept of originality and “an artistic career” is queried. The peculiar nature of Dylan’s relationship with chronology was set as early as 1964 with the assertion of “My Back Pages” that “I was so much older then, I’m younger than that now.” Dylan’s project has always been one of destabilising and productively representing the self (rather than himself), anticipating how his work is received and demolishing that reception. I analyse the patterns of revisionary disruption within Dylan’s work, at first using Edward Said’s On Late Style. Necessarily, attention then shifts toward Said’s precursor, Theodor Adorno. The study therefore contributes significantly to our understanding of Dylan, and in particular by focusing on areas of his work that have sometimes seen as aberrations (his Christmas album, his cover version of Sinatra, his much-derided Self Portrait), but it also adds to the discourse on late style by demonstrating how lateness is not a matter of age, but of decision and commitment on the part of an artist. It also questions Adorno’s insistence that such matters are limited to the domain of classical forms of expression, and develops Perry Meisel’s related conception of canonicity contra Adorno. Dylan’s late style disagrees with Said and Adorno on lateness, particularly in how they relate it to idea of biological aging. While the older Dylan may be seen to be in possession of a late style, the Dylan who arrived on the scene in the 1960s did so too. He has always disrupted how others might see him, and has always run the risk of destroying his own settled reputation. Dylan has always played Prospero, therefore, he is (and was) always late.