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10 Greatest Bob Dylan Songs

“Every songwriter after him carries his baggage,” Bono writes. “This lowly Irish bard would proudly carry his baggage. Any day.”

10, Greatest, Bob Dylan, Songs

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From the Sixties protest anthems that made Bob Dylan 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. 

See our picks for his 10 greatest songs below, and for more, check out our epic list of his 100 greatest songs right here.

'Just Like a Woman' bob dylan 1966

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4

‘Just Like a Woman’

Happy Birthday BobBlonde On Blonde, 1966

Dylan's finest ballad is not a love song. "Just Like a Woman" is a complex portrait of adoration and disappointment, written as vengeance but sung as regret. Dylan never revealed a specific inspiration for the woman indicted. (Dylanologists often cite Andy Warhol's star-crossed protégée Edie Sedgwick.) But the song is more about his own turbulent lessons in romance — the giving, taking and leaving. It is also Dylan's first great country-rock performance. Dylan was making thunder and headlines onstage that year with the Hawks, but he cut this song with Nashville session cats who heard and heightened his tangle of rapture and despair. "There's a lifetime of listening in these details," songwriter Jimmy Webb said. "I still marvel at what an absolutely stunning piece of writing it is."

 

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3

‘Tangled Up in Blue’

Happy Birthday BobBlood On the Tracks, 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 both utopian and broken promise. His plaintive vocal and the fresh-air picking of the Minneapolis session players, organized by his brother, David Zimmerman, 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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2

‘A Hard Rain’s A-Gonna Fall’

Happy Birthday BobThe Freewheelin' Bob Dylan, 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."

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"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."

Photograph by Jerry Schatzberg/TrunkArchive.com

1

‘Like a Rolling Stone’

Happy Birthday BobHighway 61 Revisited, 1965

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 on display here cracks open songwriting for a generation and leaves the listener on the canvas. "Like a Rolling Stone" is the birth of an iconoclast that will give the rock era its greatest voice and vandal. This is Bob Dylan as the Jeremiah of the heart, torching romantic verse and "the girl" with a firestorm of unforgiving words. Having railed against the hypocrisies of the body politic, he now starts to pick on enemies that are a little more familiar: the scene, high society, the "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 vanity of that time, the idea that you had a better value system if you were wearing the right pair of boots.

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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 would later admit to imitating. 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 the question "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 just 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 for all the tirading, 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 and immediate 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 — when those two things are in perfect balance — is when everything happens with rock & roll. And that's what Dylan achieved in "Rolling Stone." I don't know or 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 real thrill for me was that "once upon a time" in the world, a song this radical was a hit on the radio. The world was changed by a cranky voice, a romantic spirit, somebody who cared enough about an unrequited love to write such a devastatingly caustic 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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