Examining the reasons why Bob Dylan was awarded the 2016 Nobel Prize for Literature, the author points out that the most salient was that Dylan represented the cultural idol of the American 1960s. In other words, his selection for the award can be attributed largely to a pervasive structure of feeling in Western society that had been shaped by widely-shared post-Sixties narratives, especially in the literary field. Next, an analysis of Dylan’s most famous ballads shows that Dylan himself created post-Sixties narratives. This puts him in a role parallel to the New York intellectuals. Dylan and the New York intellectuals are not only important Sixties’ trope-makers, but also masters who were adept at using popular vernacular to reach wide audiences. Articulating political concerns is another shared characteristic of their post-Sixties narratives. To both Dylan and the New York intellectuals, post-Sixties narratives have served as an effective device to engender a desire for social change in American society. Viewed in a certain light, Dylan is himself, oddly, one of the New York intellectuals.