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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

3

“Tangled Up in Blue” (1975)

"[This song] took me 10 years to live, and two years to write," Dylan often said before playing "Tangled Up in Blue" in concert. His marriage was crumbling in 1974 as he wrote what would become the opener on Blood on the Tracks and his most personal examination of hurt and nostalgia. Dylan's lyrical shifts in perspective, between confession and critique, and his acute references to the Sixties experience evoked a decade of utopian dreams and broken promise. His plaintive vocal and the fresh-air picking of the Minneapolis session players hearkened to an earlier pathos: the frank heartbreak and spiritual restoration in Appalachian balladry. Dylan has played this song many different ways live but rarely strays from the perfect crossroads of this recording, where emotional truths meet the everlasting comfort of the American folk song.

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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

2

“A Hard Rain’s A-Gonna Fall” (1963)

The greatest protest song by the greatest protest songwriter of his time: a seven-minute epic that warns against a coming apocalypse while cataloging horrific visions – gun-toting children, a tree dripping blood – with the wide-eyed fervor of John the Revelator. "Every line in it is actually the start of a whole song," Dylan said at that time. "But when I wrote it, I thought I wouldn't have enough time alive to write all those songs, so I put all I could into this one."

The threat of nuclear war was in the air at the time, as other songs from the Freewheelin' sessions – including "Talkin' World War III Blues" and the anti-fallout-shelter rant "Let Me Die in My Footsteps" – make clear. But this rain was abstract rather than literal. "It's not the fallout rain," Dylan said. "I just mean some sort of end that's just gotta happen."

"A Hard Rain's A-Gonna Fall" – that "a-gonna" was the young Dylan's Woody Guthrie fixation popping out again – began life as a poem, which Dylan likely banged out on a typewriter owned by his buddy (and fellow Greenwich Village dweller) Wavy Gravy. Dylan debuted the song at Carnegie Hall in September 1962, when he was part of a folk-heavy bill in which each act got 10 minutes: "Bob raised his hand and said, 'What am I supposed to do? One of my songs is 10 minutes long,'" said Pete Seeger, the concert's organizer.

"A Hard Rain" is the first public instance of Dylan grappling with the End of Days, a topic that would come to dominate his work. But the tumbling verses of "A Hard Rain" culminate not in catastrophe but in Dylan describing his task as an artist: to sing out against darkness wherever he sees it – to "tell it and think it and speak it and breathe it" until his lungs burst. "It's beyond genius," says the Grateful Dead's Bob Weir. "I think the heavens opened and something channeled through him."

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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

1

“Like a Rolling Stone” (1965)

Bono: That sneer – it's something to behold. Elvis had a sneer, of course. And the Rolling Stones had a sneer that, if you note the title of the song, Bob wasn't unaware of. But Bob Dylan's sneer on "Like a Rolling Stone" turns the wine to vinegar.

It's a black eye of a pop song. The verbal pugilism cracks open songwriting for a generation and leaves the listener on the canvas. "Rolling Stone" is the birth of an iconoclast that will give the rock era its greatest voice and vandal. This is Dylan as the Jeremiah of the heart. Having railed against the hypocrisies of the body politic, he starts to pick on enemies that are a little more familiar: the scene, high society, "pretty people" who think they've "got it made." He hasn't made it to his own hypocrisies – that would come later. But the "us" and "them" are not so clearly defined as earlier albums. Here he bares his teeth at the hipsters, the idea that you had a better value system if you were wearing the right pair of boots.

For some, the Sixties was a revolution. But there were others who were erecting a guillotine in Greenwich Village not for their political enemies, but rather for the squares. Bob was already turning on that idea, even as he best embodied it, with the corkscrew hair Jimi Hendrix imitated. The tumble of words, images, ire and spleen on "Rolling Stone" shape-shifts easily into music forms 10 or 20 years away, like punk, grunge or hip-hop. Looking at the character in the lyric, you ask, "How quickly could she have plunged from high society to 'scrounging' for her 'next meal'?" Perhaps it is a glance into the future; perhaps it's fiction, a screenplay distilled into one song.

It must have been hard to be or be around Dylan then; that unblinking eye was turning on everybody and everything. But the real mischief is in its ear-biting humor. "If you ain't got nothing, you got nothing to lose" is the T-shirt. But the line that I like the best is "You never turned around to see the frowns on the jugglers and the clowns/When they all did tricks for you/You never understood that it ain't no good/You shouldn't let other people get your kicks for you."

The playing on this track – by the likes of guitarist Mike Bloomfield and keyboardist Al Kooper – is so alive that it's like you're getting to see the paint splash the canvas. As is often the case with Bob in the studio, the musicians don't fully know the song. It's like the first touch. They're getting to know it, and you can feel their joy of discovery as they're experiencing it.
When the desire to communicate is met with an equal and opposite urge not to compromise in order to communicate is when everything happens with rock & roll. And that's what Dylan achieved in "Rolling Stone." I don't particularly care who this song is about – though I've met a few people who have claimed it was about them (some who weren't even born in 1965). The thrill for me was that "once upon a time," a song this radical was a hit on the radio. The world was changed by somebody who cared enough about an unrequited love to write such a devastating put-down.
I love to hear a song that changes everything. That's the reason I'm in a band: David Bowie's "Heroes," Arcade Fire's "Rebellion (Lies)," Joy Division's "Love Will Tear Us Apart," Marvin Gaye's "Sexual Healing," Nirvana's "Smells Like Teen Spirit," Public Enemy's "Fight the Power." But at the top of this dysfunctional family tree sits the king of spitting fire himself, the juggler of beauty and truth, our own Willy Shakespeare in a polka-dot shirt. It's why every songwriter after him carries his baggage and why this lowly Irish bard would proudly carry his luggage. Any day.

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