19. Bob Dylan, "Ballad of a Thin Man" (1965)

(listen)

The fact is I could have taken any song from Highway 61 Revisited and put it approximately here, or spread them all up and down this list—it's my favorite album and has been for as long as I can remember and somehow it stays fresh and bracing every time I come back to it, even broken down to constituent parts. But this is the song that I recall amazing me first and most, doing things I didn't know could be done in a song or anything like it. It proceeds like a dream, a nightmare of powerlessness from the point of view of the tormentor, existing languidly within the smoky music of that remarkable session. It's at once funny and caustic. I laughed at parts of it like it was a stand-up routine: "And you say 'What does this mean?' and he screams back 'You're a cow / 'Give me some milk or else go home.'" And I gulped at others, recognizing myself in Mr. Jones nearly as much as I recognized myself (or the desire for it to be myself) in the ultra-cool uber-hip insider singing the song. One has only to see Dylan's treatment of Donovan in the D.A. Pennebaker documentary Don't Look Back to realize that a good deal of the time, at this point in his career, he was trading in the kind of alienating clique-mongering that's more appropriate to junior-high kids (and there are any number of reasonable explanations for that, given the totality of his experience at the time). Yet "Ballad of a Thin Man" is as seductive a portrait of the impulse as can be found anywhere, and a fine example of the pure blasts of dazzling language that populate that album too. It still amazes me—even knowing that I have become someone, like Mr. Jones, who has been through all of F. Scott Fitzgerald's books.