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100 Greatest Bob Dylan Songs

From “Just Like a Woman” to “John Wesley Harding,” we count down the American icon’s key masterpieces

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EXCLUSIVE; SPECIAL RATES APPLY. Bob Dylan in his Greenwich Village apartment just a few months before he would release his self-titled debut album. (Ted Russell/Polaris) /// Bob Dylan

Ted Russell/Polaris

As Bob Dylan turns 75, he shows no signs of slowing down. The American icon is gearing up for a summer tour with longtime friend Mavis Staples and has just released Fallen Angels, his 37th LP and second straight Sinatra-inspired album of American Songbook classics. For generations to come, other artists will be turning to Dylan’s own catalog for inspiration. From the Sixties protest anthems that made him a star through to his noirish Nineties masterpieces and beyond, no other contemporary songwriter has produced such a vast and profound body of work: songs that feel at once awesomely ancient and fiercely modern. Here, with commentary from Bono, Mick Jagger, Lenny Kravitz, Lucinda Williams, Sheryl Crow and other famous fans, are Dylan’s 100 greatest songs – just the tip of the iceberg for an artist of his stature.

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EXCLUSIVE; SPECIAL RATES APPLY. Bob Dylan in his Greenwich Village apartment just a few months before he would release his self-titled debut album. (Ted Russell/Polaris) /// Bob Dylan

Ted Russell/Polaris

54

“4th Time Around” (1966)

What exactly inspired "4th Time Around" is one of the great Dylan mysteries. The melody and story line are a direct takeoff of the 1965 Beatles song "Norwegian Wood" – among the band's first songs with a clear Dylan influence. Was the line "I never asked for your crutch, now don't ask for mine" a warning to stop ripping him off? Dylan's never said, but three months after he recorded it, he went on a famously stoned limo ride with John Lennon around London and didn't seem to be harboring any malice. The next year he released John Wesley Harding, which has what appears to be an upside-down image of the Beatles hidden in a tree on the cover – but that's another mystery.

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EXCLUSIVE; SPECIAL RATES APPLY. Bob Dylan in his Greenwich Village apartment just a few months before he would release his self-titled debut album. (Ted Russell/Polaris) /// Bob Dylan

Ted Russell/Polaris

53

“When I Paint My Masterpiece” (1971)

Probably the least irritating song ever written about the life of a superstar on the road, Dylan's studio version surfaced in late 1971 among the unreleased material on Greatest Hits Vol. II. Produced by Leon Russell, the track lays gospel piano chords under a lament about awaiting inspiration in between gigs, aimless wandering, fame-related hassles and "a date with Botticelli's niece." The definitive version was recorded live with the Band on New Year's Eve 1971 and released on the Band's Rock of Ages. "Sailin' round the w