14. "Highway 61 Revisited" (1965)
"I always felt like I'd started on it, always had been on it, and could go anywhere from it," Dylan said of Highway 61, which runs from his native Minnesota down to New Orleans. Here, he proved just how far he could take it. Recorded in a marathon session that also spawned "Just Like Tom Thumb's Blues," "Ballad of a Thin Man" and "Queen Jane Approximately," the galloping title track from 1965's electric breakthrough Highway 61 Revisited is Dylan in frizzed-out jeremiad mode. He leads a series of star-crossed characters (most famously, God and Abraham) down to America's "blues highway," while spitting venom at a series of American hypocrisies (phony patriotism, crass commercialism). Session musician Al Kooper claimed he lent Dylan the police whistle that jarringly kicks off and closes the song, instructing him to use it instead of his harmonica. "A little variety for your album," he told Dylan at the time. "Suits the lyric better."