Bob Dylan's 10 Best Songs: Critic's Picks

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Bob Dylan poses for a portrait with his Gibson Acoustic guitar in September 1961 in New York City.

Let’s start by acknowledging the impossibility of the task. Name the 10 best Bob Dylan songs? Why not try and pick the 10 best stars in the sky? Or maybe the 10 best numbers? You see the problem here.

For more than half a century, Dylan has served as rock and folk music’s poet laureate, writing and performing dozens and dozens of classic songs -- hundreds of songs overall -- and any number of them could easily populate this list. 

As of June, Dylan is a Nobel laureate as well, having been given this year’s award for literature. Dylan seemed as skeptical of his receiving the Nobel Prize as he has been of other honors that have come this way. Others were skeptical, too, wondering if songs could really be construed as literature. But that is an argument for another time and place. What is certain, though, is that Dylan and his songs changed the culture. People looked to Dylan as a leader, a seer, a messiah, even, and he rejected every such overture. 

Yet his songs led the way, and they have endured -- as has Dylan himself. As he sang in 1975 on “Tangled Up in Blue," “But me, I’m still on the road/Headin’ for another joint" -- which he is, as his Never Ending Tour continues to roll on indefinitely. 

Is "Tangled" one of his all-time best? What about the rest of those listed below? We feel they are right now; tomorrow it might be a different story. Your list might be different, and probably is. Of Dylan fans, it can accurately be said -- and was by the man himself, again via "Tangled" -- “We always did feel the same/We just saw it from a different point of view.” 

10. Bob Dylan - "Not Dark Yet"

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After releasing his 1997 album Time Out of Mind, Dylan went on to record more original work, as well as his more recent series of covers albums. But had “Not Dark Yet” served as his farewell, it would have been perfect. It’s a song about nearing the end of life, having seen too much and having been let down by too many too often; about a world weariness that can barely be borne. “Feel like my soul has turned into steel,” Dylan sings. “I’ve still got the scars that the sun didn’t heal.” 

Of course, this Bob Dylan song nearly did serve as a final statement. Several months before Time Out of Mind was released, Dylan was laid low by a life-threatening bout with pericarditis, brought about by the fungal infection histoplasmosis. “I really thought I’d be seeing Elvis soon,” he said in a statement. Dylan beat the reaper, but the haunted, exhausted, yet elegant and profound “Not Dark Yet” stands as one of his most moving testaments. 

9. Bob Dylan - "Every Grain of Sand"

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Dylan’s late-‘70s/ early 80’s Christian trilogy of albums marked one of the most controversial periods of his career. Many of the songs from that period are damning, didactic and dogmatic. Not “Every Grain of Sand,” in which Dylan is prayerful and open-hearted, seeking transcendence in the God-created cathedrals of nature and the chambers of his own heart. Or as he puts it: “In the fury of the moment I can see the Master’s hand/ In every leaf that trembles, in every grain of sand.” 

8. Bob Dylan - "All Along the Watchtower"

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A maximalist at heart -- so many of his songs feature verse upon verse, absolute cascades of words and images -- Dylan is at his minimalist best here. Just 12 lines in three verses, painting a stark scenario of a joker (a likely stand-in for Dylan himself), who is being robbed by “businessmen [who] drink my wine [and] plowmen [who] dig my earth” (read: music industry weasels), and one of the thieves -- whose message to the joker is essentially, “Chill.” 

Originally an acoustic track on his John Wesley Harding album, “Watchtower” may have never reached its full potential or popularity if not for an electric -- and electrifying -- cover by Jimi Hendrix, which so impressed Dylan that he began performing it a la Hendrix, giving the song an even heavier sense of foreboding, and turning it into one of Dylan’s most reliable concert staples. 

7. Bob Dylan - "Subterranean Homesick Blues"

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The lead track on Dylan’s 1965 album Bringing It All Back Home, and his first top 40 hit on the Billbaord Hot 100, “Subterranean Homesick Blues” presented Dylan to the world as a rocker.

Fueled by his rock and jazz forebears (“It’s from Chuck Berry, a bit of ‘Too Much Monkey Business’ and some of the scat songs of the ‘40s,” Dylan told Robert Hilburn), beat poetry (that’s Allen Ginsberg holding court in the background of Dylan’s cue-card-flipping film clip of the song, essentially one of the very first music videos), and whatever “medicine” Johnny was mixing up in the basement, the song is rollicking mix of absurdity, wordplay, and sloganeering (“Don’t follow leaders/Watch the parking meters”). Like several of the talking blues songs from his earlier albums, it also showed that the writer of poetic epics and hyper-serious protest songs had a sense of humor.

6. Bob Dylan - "Visions of Johanna"

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One of Dylan’s most enigmatic songs -- no small feat -- and one of his most densely poetic, Blonde on Blonde's “Visions” is a rich subject for debate among Dylanophiles. At its most basic, the song contrasts two women: “Louise,” who is nothing special, apparently, but is available (“Louise, she’s all right, she’s just near,” Dylan sings), and Johanna, who represents some kind of unattainable perfection -- of love or art or…something. 

At the same time, Dylan takes us on a phantasmagorical tour of low-rent urban life, detailed with the coughing pipes of a cheap hotel (likely the infamous Chelsea, where Dylan composed the song), and various street characters (the “all-night girls,” “little boy lost,” a peddler, a fiddler, “Madonna” (no, not that one)-- it’s quite a cast). Rich in gritty detail and thick with meaning that, like Johanna herself, is just out of reach, “Visions” is one of Dylan’s most puzzling yet tantalizing creations. 

5. Bob Dylan - "A Hard Rain’s A-Gonna Fall"

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Written at the height of the Cold War and in the midst of the Cuban Missile Crisis, “Hard Rain” is typical in that the song is completely of its time and -- sadly -- all too relevant yet today. But its Book of Revelations-style imagery and apocalyptic message rings all too true in an era of natural disasters and endless war. This Bob Dylan song is stark and relentless -- nearly seven minutes of intensity and tension brought home with just voice and guitar. “I’ll tell it and think it and speak it and breathe it,” he sings. “And reflect it from the mountain so all souls can see it.” 

It’s unclear whether the hard rain that’s promised in the chorus is atomic fallout or a Noah-like flood, but it scarcely matters. It’s coming. 

4. Bob Dylan - "Tangled Up in Blue"

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Dylan has said in concert that “Tangled Up in Blue” took him “10 years to live and two years to write.” Because he generally says so little by way of introducing his songs, those words carry weight. But there’s always been some doubt as to which details of the song are autobiographical and which are poetic fancy. Dylan has further muddied the waters by shifting points of views in the song and continually changing the lyrics.

But the song excels and intrigues in all its forms and marks a farewell to a relationship as well as the bygone era of the ‘60s. “The only thing he knew how to do was keep on keepin’ on,” Dylan sings of his protagonist. And likely himself as well. 

3. Bob Dylan - "It’s Alright Ma, (I’m Only Bleeding)"

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The problem with positing yourself as a teller of truth and a chronicler of others hypocrisies is that it sets you up for a fall -- people who live in glass houses, etc. -- and Dylan must have been aware of that. Yet “It’s Alright Ma” delivers withering fusillades of accusations and vitriol in all directions, consequences be damned. It is irresistible for its imagery and alliterative poetry, but set a high standard that even Dylan himself could not sustain. “Try to sit down and write something like that,” he told 60 Minutes in 2004. “I can do other things now. But I can’t do that.” 

2. Bob Dylan - "Like a Rolling Stone"

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The snare drum shot that opens the song is the sound of a gauntlet being thrown down. “Like a Rolling Stone” is a challenge, on every level, to everyone who hears it. Commercially, it became Dylan’s biggest hit to date, despite being a single that exceeded six minutes in length. Sonically, it’s slow, majestic chord progression (borrowed from Ritchie Valens’ “La Bamba,” of all things), swooped and soared, led by Al Kooper’s unschooled organ playing and Mike Bloomfield’s piercing guitar, over which Dylan alternately sneered and brayed the famous chorus, “How does it FEEEEEL?” 

A blistering attack on the privileged, jaded “Miss Lonely” -- and, by extension, a generation of hipsters and hangers-on, the sorts of people of which Dylan had already had his fill – “Rolling Stone” is as naked and savage a cry of “Fuck off” as exists in the annals of popular song. 

1. Bob Dylan - "Blowin’ in the Wind" 

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If Dylan’s claim that he wrote “Blowin’ in the Wind” in 10 minutes is true, you’d be hard pressed to find another 10 minutes in any songwriter’s career that were better spent. A deeply philosophical, even spiritual song, “Wind” is a series of Zen koan-like questions resolved in a chorus that contends that the answer is unknowable -- or knowable, perhaps, but just beyond our reach, like a “restless piece of paper” blowing down the street, as Dylan once said. Its melody is borrowed from an African-American spiritual, “No More Auction Block,” a fact some would find damning, but such is the folk process that Dylan has worked within his entire career. 

It took Peter, Paul & Mary’s honey-harominied version to break Dylan’s rough-hewn song open, and it broke big, with the cover selling over 300,000 copies in a week (eventually topping a million) and landing it at No. 2 on the pop chart. Since then it’s been sung by countless singers at coffee houses, protest marches, and gatherings of all sorts. It’s been covered countless times, by artists as wildly various as Duke Ellington, Flatt & Scruggs, Stevie Wonder, Spike Jones, Etta James and Cher. 

Of course, it also became an anthem of the Civil Rights Movement. Peter, Paul & Mary sang it on the steps of the Lincoln Memorial during the March on Washington the day Martin Luther King delivered his “I Have a Dream” speech. Sam Cooke put it in his own repertoire, and later answered it with a civil rights anthem of his own, “A Change Is Gonna Come.” 

The song has hope, a hint of mystery, and is source of inspiration to others; that’s Dylan at his absolute best. 


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