So, here we’ve finally arrived: “Bob Dylan’s 10 Best Songs,” the Iraq Invasion of long-form rock journalism. Uncalled for and utterly unwinnable, contending with a thousand-song catalog so rich, varied, mysterious, and fraught with social and artistic context that the very notion of its distillation courts nothing less than madness. Why not rank Shakespeare’s 10 best quotations or Matisse’s 10 best line strokes?
We proceed knowing that there is no one right answer, or even 10 right answers, in highlighting the best moments of a legendary five-decade career that will surely endure the ages. And it hardly feels like just ranking one artist — there have been as many Dylans as there have been seismic shifts in our cultural landscape over the course of his career. From his initial emergence as an early-’60s folky-urchin to his current status as great, debauched last-legs bluesman, Dylan has somehow always remained a preeminent bellwether for a searching society.
In the early years of Dylan’s incandescent genius, great songs came fast and furious — so many between the period of 1963’s Freewheeling Bob Dylan through 1967’s John Wesley Harding that they could fill multiple jukeboxes with unimpeachable classics. Only a few of these ’60s songs are on this list, however, because a kind of curious thing occurred as the artist progressed through the obstacles of his young stardom into different iterations of personae and style. The ’70s were a period of professional and personal upheaval, as well as heavy experimentation, and at times Dylan could seem unmoored and veritably unstable. The ’80s were worse: Plagued by flagging confidence, industry pressure and poor judgment of every sort, the man who could very easily be argued the greatest living artist made some of the worst music of his era. By the time of his gradual regeneration and startlingly fully formed reimagination of sound and image in the late 1990s he had been savagely through the ringer and emerged as the kind of “soul survivor” the Stones once envisioned in 1972.
Dylan’s middle decades — the wilderness years between his ’60s supernova exertions and his post-millennial stance as icy cool bluesman — are in retrospect the most fascinating and important of his career. The folk, country, and rock traditions Dylan loved and inherited as a teenaged phenom had not much history with, and very little use for, middle age. By the time a 20-year-old Dylan had traveled east to New York and had begun making regular pilgrimages to a grim state hospital to see his idol Woody Guthrie, the legendary folk singer was nearing his painful death from Huntington’s disease at the young age of 55. Hank Williams, Buddy Holly and Eddie Cochran had all met ugly early deaths, and Elvis Presley was already commencing his long, sad slide into self-parody.
As the defiantly unwilling but nevertheless typecast face of a ’60s counter culture, Dylan confronted a remarkable challenge in transitioning from his l’enfant terrible, “voice of a generation image” into the kind of varied, intensely personal and visionary artist he had always imagined he might become. It is during the 1970s and ’80s that he not only authored the lion’s share of his greatest songs, but perhaps in some ways made his most enduring contribution by providing a credible, uncompromising pathway for the rock idiom to exist as something more than a phenomenon of ephemeral youth culture.
The following list of 10 songs does not reflect the most famous Bob Dylan material. Certain songs not included on this list are infinitely better known, and have deeper currency and resonance in our culture, for better or worse.
We have chosen 10 songs which in our judgment offer the best summation of the artist’s great themes: love of freedom and hatred of oppression, the profound belief in higher powers both musical and spiritual, and the often devastating journey from innocence to experience. They represent the full palette of compassion, spite, historicity, humanity, comedy, and bitterness that informs the work of this frighteningly gifted (and sometimes just frightening) artist. It’s not so much that reasonable people could disagree — reasonable people probably must disagree. But take these 10 choices for what they’re worth: a brief snapshot rendering the passionate work of one of music’s great visionaries.
10. “Idiot Wind” (from Blood On The Tracks, 1975)
The devastatingly bitter and resigned breakup account from 1975’s perfectly named emotional apocalypse Blood On The Tracks finds the artist both terrorized by the ramifications of an impending divorce from his wife and mother of his children, and brilliantly extrapolating upon the failed promise of that union to represent the failure of the dreams of the ersatz “Peace And Love” generation. Crushingly, Dylan sees himself as having taken on an image too large and unwieldy for even his once-beloved spouse to fathom: “Even you yesterday/ had to ask me where it was at/ I can’t believe after all these years/ you didn’t know me any better than that.” The hurt and alienation Dylan expresses is tellingly and appropriately panoramic, casting a net large enough to characterize social dysfunction ranging from “the Grand Coulee Dam to the Capitol.” No less than Alan Ginsberg referred to that as “the great disillusioned national rhyme.” “Idiot Wind” is ultimately an unsparingly hurtful and honest referendum of a relationship and culture in crisis.
9. “Highlands” (from Time Out Of Mind, 1997)
The remarkably brilliant 16:32 closing track on 1997’s late period masterpiece Time Out Of Mind is an audacious gambit — a stemwinding blues-based narrative reminiscent of a casually jaundiced take on previous, dislocated epics like “Stuck Inside Of Mobile With The Memphis Blues Again.” Traveling from the Scottish Highlands of the title to the run-down diners of Boston, Dylan ingeniously sketches (literally) the life of an aging legend who still dares to exist as something other than a self-caricature. By the time he encounters a youthful and insouciant waitress, the ensuing comedy is as telling as it is ingratiating and awkward. This is Dylan as beguiling self-critic –- of his age, of his legacy, and of his general worth — and it’s clear he takes to the task with a clear-eyed understanding.
8. “Gotta Serve Somebody” (from Slow Train Coming, 1979)
Dylan’s turn towards evangelical Christianity on 1979’s Slow Train Coming caught a great deal of his audience off guard, and more than a few critics and fans were stunned and appalled to the point of ridicule. In fairness, this seemingly strange gesture was actually consistent with a longstanding tendency on Dylan’s behalf to throw the occasional wicked curveball at his audience. But, under close examination, was it really such a curveball? Biblical concerns have preoccupied Dylan for at least as long as the Old Testament-styled parable “Hard Rain.” In the case of “Gotta Serve Somebody,” Dylan brings to bear a funky, funny, and poignant track filled with self-effacing jokes and the suggestion that there is always a power to honor someone greater then oneself. Observers at the time might have been alarmed, but in truth this is the same old Dylan — catchy, contentious, insightful and morally probing.
7. “Highway 61 Revisited” (from Highway 61 Revisited, 1965)
On an album stocked with brilliant and deservedly fetishized warhorses like “Ballad Of A Thin Man” and “Like A Rolling Stone,” the unmitigated highlight is the title track — a caustic, three-and-a-half-minute no-holds-barred take on amphetamine blues that sets the template for pub and punk rock a full 10 years before their respective flowerings. Here, Dylan’s comic fearlessness in retelling ancient tales of Old Testament insanity juxtaposed alongside savage indictments of contemporary hucksters reflects modern society’s seemingly unchecked capacity for greed and alludes to the sort of no-cost-too-great cruelty that has become too common in Western attitudes towards war. “Yes, I think it could be very easily done…”
6. “Changing Of The Guards” (from Street Legal, 1978)
The lovely, horn-flecked lead track from what is perhaps Dylan’s most difficult and dense release is a remarkably compelling and evocative allegory of Dylan’s experience in the music industry, as well as a clear statement of his intentions to defy any existing expectations going forward. Unfolding like an old parable or a recent video game, he describes his circumstance without sentiment or apology, informing his would-be masters in the industry that he will no longer serve their agenda. “Gentlemen, I don’t need your organization/ I’ve moved your mountains and marked your cards/ But Eden is burning, either get ready for elimination/ Or else your hearts must have the courage for the changing of the guards”. As Dylan has continued to flourish and the industry continues to wither, it is difficult to not see these words as prophetic.
5. “Visions Of Johanna” (from Blonde On Blonde, 1966)
The intensity and wonder of “Visions Of Johanna” is not an easy thing to metabolize. Dylan was amongst the first songwriters to acknowledge the modern poetry of the Beats as well as earlier inspirations like T.S. Eliot and Dylan Thomas. As an audience, this is the song in which we experience the blossoming of these influences. Set to a profoundly moving melody, “Visions Of Johanna” is an abstract and complicated three-way romance between the singer, the titular Johanna, and the mysterious Louise. It is a vaguely psychedelic, impressionistic forerunner to the more exacting tripartite romance of “Tangled Up In Blue.” But even at this relatively embryonic stage, Dylan has achieved heights of transcendent brilliance. Indeed, British Poet Laureate Andrew Morton called “Visions Of Johanna” the “best song lyric ever written.”
4. “Blind Willie McTell” (from The Bootleg Series Vols. 1-3, 1991)
One of the persistent mysteries amongst Dylan fans has involved the question of why he has frequently left his best material off of various albums, only to be revealed as revelatory portions of later collections. Never has this question reached a fever pitch quite like in the case of “Blind Willie McTell,” a stunningly prophetic and bracing song, lost from the original track listing of 1983’s Infidels and later retrieved on The Bootleg Series Vol. 1. Regardless of its provenance, “Blind Willie McTell” remains one of the artist’s most chilling and moving compositions, suggesting in its opening lines a national corruption both deep and historic. Over a lovely and brooding minor key melody line, Dylan acknowledges the awful toll taken on African Americans, including his foremost musical heroes, as well as a through line that includes his own people’s oppression: “Seen the arrow on the doorpost/ saying ‘This land is condemned’/ all the way from New Orleans/ to Jerusalem.” Painful and cathartic stuff.
3. “It’s Alright, Ma (I’m Only Bleeding)” (from Bringing It All Back Home, 1965)
In a series of revealing interviews with Martin Scorsese in his 2005 documentary No Direction Home, Dylan characterized this stunning 1965 composition as the kind of thing that he could once render unconsciously, but seemed mysterious to him in his older vintage. Like an aging athlete puzzling over the diminishment of his erstwhile formidable powers, Dylan’s explanation seems utterly too plausible. Over the top of some truly astonishing guitar playing, this is a song that piles one priceless aphorism after the next: “He not being busy being born is busy dying,” “Even the president of the Unites States sometimes must have to stand naked,” and, perhaps the most painful truth: “It’s easy to see/ not much is really sacred.” This is early Dylan at his level best, challenging every facet of the established order with candor and truth. Though he was never a capital-R “Revolutionary”, it is easy to see the attraction he brought to bear from those hoping to disrupt the social order. But as far as Dylan goes, the hippies bet on the wrong horse, and he went the other way.
2. “Tangled Up In Blue” (from Blood On The Tracks, 1975)
Arguably the saddest and most telling folk song of the past 50 years, “Tangled Up In Blue” is an impeccably rendered narrative about two lovers whose desperate affection for one another is insufficient to overcome the societal context and manifold anxieties that keep them apart. It is a complex story that tumbles one verse after the next, each iteration seeming to up the ante on loss and pain. This is a grown-up, travel-weary Dylan, no longer fueled by ideals, but still searching and dreaming of renewal. When he sings the words “All the people we used to know/ they’re an illusion to me now”, the implication could not be more clear: The ’60s were little more than a reckless, self-indulgent miasma. In the aftermath, all that is left is the painful job of attempting to manifest meaning from the shattered pieces of warped idealism gone terribly awry.
1. “Every Grain Of Sand” (from Shot Of Love, 1981)
A deep reservoir of intense spirituality has infused Dylan’s oeuvre from the very beginning. Early works ranging from “Hard Rain” to “Gates Of Eden” made clear both his familiarity with the scriptures and nerveless intent to put his own interpretations front and center in his music. Provided that context, it’s puzzling that many responded to Dylan’s overt gospel records of the late ’70s and early ’80s with slack-jawed surprise, but through it all, Dylan retained a sense of humor, irony, and reverential humility. “Every Grain Of Sand” finds a powerful man acknowledging a devastating vulnerability and profound sense of awe as he imagines the complex minutiae of a vast universe that even a man of his considerable gifts cannot understand. For all of his ironclad insights, this act of conspicuous wonderment feels like his bravest acknowledgment. He who seemed to see so far really knew nothing at all.
Listen to the Spotify playlist here.