5. "All Along the Watchtower" (1967)
You could say that jokes and theft are the twin poles of Dylan's art, and this 12-line masterpiece about a joker (who believes he's being robbed) and a thief (who thinks everything's a joke) penetrates to the core of his work. "Watchtower" is among Dylan's most haunting tunes: Built around an austere arrangement and Dylan's spooked croon, it starts like a ballad that's going to go on for a long while. But as soon as the joker and the thief get their opening statements, the song ends with an ominous image – two riders approaching – leaving listeners to fill in the blanks.
Jimi Hendrix's reading of "Watchtower" is one of the few Dylan covers that has permanently affected the way Dylan himself plays the song. Hendrix started recording his cover within weeks of John Wesley Harding's release, fleshing out the song into something stunningly intense. "He played [my songs] the way I would have done them if I was him," Dylan later said of Hendrix.