Bob Dylan came through the campus where I resided way back in the sixties (1964). I met him and thought then he was a sort of traveling philosopher, not really participating in the culkture directly but ready to reflect societal currents with his muse. Subsequently, many thought of him as an anarchist; he never was or would be. Some thought of him as a hippie; he wasn’t committed to dropping out, just the opposite! Some thought of him as a doper; he wasn’t. A very few recognized him for what he really was and still is, though not as active now; he was in fact a philospher with music as a means of expression, and he was going to ride out the changes whatever they were and remain an opiner not a participant.
You summed that up very well... I grew up thinking he was one of those “Counter-Culture 1960s Revolutionaries” (I was born in 1972). Now that I am older, have read a lot more, and understand more of the truth behind the facade of the “hippies”, I have found a lot of things I believed in this area were very wrong. My thoughts about Dylan being one of them... As you said, he is a philosopher, a thinker, and someone who has an incredible gift for imagery and metaphor within music. Fascinating guy, Dylan is. :)