Home Music Music Lists

100 Greatest Bob Dylan Songs

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

100; Greatest; Bob Dylan; Songs; Rolling Stone; List; Music

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.

Play video

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

56

“You’re Gonna Make Me Lonesome When You Go” (1975)

Jim James: Blood on the Tracks has always been one of my favorite Dylan records – it's the classic tough-love album to turn to when you're feeling kind of alone. "You're Gonna Make Me Lonesome When You Go" might win my repeat-listening award. I don't know if it's just the acoustic guitar and the bass, the way they work together rhythmically, but when I hear the song, it's just the essence of love. He's describing everything so viscerally. I can almost smell the trees and different people I've known over the years, the flowers, the sunlight – the way things look when you're falling in love and how that turns in on itself when you have to leave or move on or life changes you or changes the other person. He's reflecting on it in such a beautiful way, saying that person will always be a part of him. He'll see her everywhere.

Play video

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

55

“If Not for You” (1970)

After the conceptual and critical disaster that was Self-Portrait (Rolling Stone review: "What is this shit?"), fans wondered if Dylan had lost it. They didn't wonder long – New Morning, released four months later, opened with this lovely little country-rock tune. "I wrote the song thinking about my wife," Dylan said, and its lyrics are about domesticity and gratitude. Hearing the cockiest songwriter alive showing a little humility for a change is a treat.

Play video

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.

Play video

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 world in a dirty gondola," he hollered, "oh, to be back in the land of Coca-Cola!" wringing more emotion out of a brand name than anyone before or since.

Play video

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

52

“Tears of Rage” (1975)

This mesmerizing ballad first came to the world's attention as the opening track on the Band's 1968 masterpiece, Music From Big Pink. There it is sung with agonizing grace by keyboardist Richard Manuel, who co-wrote the song with Dylan during the 1967 sessions at Big Pink. When The Basement Tapes officially came out in 1975, a version with Dylan singing lead came to light. Like so many of the songs Dylan wrote at Big Pink, "Tears of Rage" is elliptical, a string of casually surreal images that draw on the Bible and, in this case, Shakespeare's King Lear. Its tale of generational strife, tone of betrayal and opening reference to Independence Day suggest that the culture wars over Vietnam and civil rights were also on Dylan's mind. The song's repeated reminders that "life is brief" rise above cliché to a desperate moral calling, an insistence that, whatever our differences, our shared mortality must make for compassion.

Play video

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

51

“Things Have Changed” (2000)

In 2001, when Dylan accepted his one and only Oscar for this contribution to the Wonder Boys soundtrack, he thanked "the members of the Academy who were bold enough to give me this award for … a song that doesn't pussyfoot around nor turn a blind eye to human nature." That's one way of putting it: For all its offhand jokes ("gonna dress in draaag," he rasps at one point), "Things Have Changed" is one of the bitterest songs in Dylan's entire catalog. It's also a harsh riposte to many of his own earlier political songs, with their longing for social justice and societal progress; "I used to care," he sings with unmistakable intent. "But things have changed." As the title suggests, it's basically the evil twin of "The Times They Are A-Changin'."

Show Comments