It's interesting tho re all the discussion on boomers and Bobby Dylan (maybe
@kid charlemagne has something to say here)
because Dylan's "cool" and "cool" broadly does not seem to me like permeability or openness. It is a preemptive shutting down.
Dylan was incredibly internal, incredibly closed off to the world in many ways. Yes he soaked up the times and is an expert trendchaser (I mean this in the least pejorative way possible—I think he's been very open, e.g., about doing protest songs in the early 60s because "the people wanted them"). He was open to some drug experimentation, became possessed by the spirit of Christianity. I have friends who swear that marijuana works by opening you up, making you "cool" with everything. And yet something about the black-turtleneck-beatnik type broadly strikes me as closed off. I can't articulate or square it yet.