Lyric discussion by BlindBoyGrunt 

The song is a panorama of human history in the manner of medieval paintings showing the past present and future, which often used the symbol of a road, for example Breughel's "Hay Wain". Dylan also connects it to his own history and American musical history for those in the know, as his father was Abraham and Highway 61 is the road that runs from Dylan's home state of Minnesota down to the deep south where much of his music comes from. Highway 61 is the land outside quotidien society where man encounters God as in the sacrifice of Isaac by Abraham - our "father in faith" and the father of Israel and thus an appropriate place wherefrom to start the story. Mack the Finger, Louis the King and "forty red white and blue shoe strings" seem to suggest the French and American revolutions which were in large part against traditional religion. "The first father" and "the second mother" suggest Adam and Eve. The "roving gambler" to me always suggests Satan, as in the Book of Job, "From going to and fro in the earth, and from walking up and down in it". Thus, again as in medieval allegory, the stage is set for a climactic confrontation ("a next world war") with Satan at the end of the world.

@BlindBoyGrunt : I'm guessing you mean the Hay Wain triptych by Hieronymus Bosch? (There's also the Hay Wain painting by John Constable, but I can't imagine how it'd fit into this.)

Not that Brueghel the Elder wasn't a painter of tremendous importance. But if you want scenarios of human cruelty (and universal absurdity) to fuel your most-peculiar nightmares? Bosch's mastery is indisputable. Or Garden of Earthly Delights: another triptych (and in this instance, title) with a brutal sting in its tail.

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