Bob Dylan’s 15 Best Albums of All Time

In honor of the folk-rock legend's birthday, revisit the most vital entries in his massive discography

Bob Dylan Best Albums
Photo by Alice Ochs/Michael Ochs Archives, illustration by Steven Fiche

    This article originally ran in 2021 and has been updated.

    Apart from, say, Frank Zappa — and that’s a rabbit hole many of us aren’t prepared to go down — there probably isn’t a more sprawling body of work in popular music than Bob Dylan’s discography. We can proclaim with even more confidence — in fact, utter certainty — that no artist has left a more exalted or scrutinized collection of albums and songs behind.

    The albums ranked in the following pages are a rare breed in that many mark their times but also mark all times. So many songs that a generation of listeners once claimed as their own have now found their way into the ears of children and grandchildren and will continue doing so for as long as albums and songs continue to be mediums we embrace.

    Revisiting these albums has been a complicated and daunting joy. Sure, we all know the euphoric sound of Al Kooper’s organ riff kick-starting “Like a Rolling Stone,” but there’s also the intense pleasure of identifying with a deep cut you’ve always skipped over in the past. Yes, there are albums here with nary a flaw on them, but sometimes that pales in comparison to the excitement of finding a great Dylan song on a terrible Dylan album. And, yes, some of Dylan’s 39 studio albums and the songs that populate them are painfully awful.


    But that comes with the territory. Dylan, if nothing else, has been, and continues to be an artist of phases — one still “busy being born” even as he turns 81 years of age on Tuesday (May 24th). That means phases where he’s penned songs that spoke to a generation and etched their words into our souls but also phases where he seemed to be just really into Jesus or wanted to follow in Sinatra’s footsteps. It’s all there — glorious and cringe-worthy — and waiting to be discovered, revisited, forgotten, salvaged, and, most of all, celebrated.

    For now, though, as we celebrate Dylan’s birthday, we’ll choose to focus on only the best of the best. Here is our definitive ranking of Bob Dylan’s 15 best records, in ascending order.

    Happy Birthday, Bob.

    — Matt Melis
    Contributing Writer

    15. John Wesley Harding (1967)

    bob dylan - john wesley harding

    Runtime: 38:24, 12 tracks

    Producer: Bob Johnston

    When I Paint My Masterpiece: Don’t beat yourself up if you don’t recognize the other three men in the photo on the album’s cover. Flanking Dylan on his left and right are sibling Bengali minstrels Luxman and Purna Das, the latter of whom has performed in more than 140 countries. Behind them is a local carpenter named Charlie Joy. Legend has it that if you turn the album cover upside down, you can see an image of The Beatles in the knot of the tree. While photographer John Berg acknowledges the resemblance, he denies that the likeness was intentional.


    It’s All Good: The gem of the collection, of course, remains “All Along the Watchtower,” an urgent tale that centers around a cryptic conversation between a joker and a thief. While fans and academics alike have tried to make sense of the song’s sparse narrative for decades, an acoustic strum, a howling harmonica, and an ominous drumbeat tell us all we need to know: that something grim — perhaps even apocalyptic — is about to go down, and the characters best get away while they still can. Jimi Hendrix would go on to transform the simple acoustic song into an expansive jam full of portent and electricity. For what it’s worth, Dylan preferred the guitar god’s version and styled his own performances of the song after Hendrix from then on.

    It Ain’t Me, Babe: Near the middle of the album sits “The Ballad of Frankie Lee and Judas Priest,” a rambling morality play that sticks out among its more laconic brethren. While Dylan does offer us a moral at the story’s conclusion, most listeners will probably echo the sentiments muttered under the breath of the boy in the penultimate stanza: “Nothing is revealed.”

    Blowin’ in the Wind: “Outside in the distance/ A wildcat did growl/ Two riders were approaching/ The wind began to howl” — from “All Along the Watchtower”


    Gone but Not Forgotten: Closing track “I’ll Be Your Baby Tonight” offers a welcome respite after 11 tracks that make you feel like you didn’t pay enough attention in Sunday school or your Bible as literature class. The ambling send-off holds no grand mysteries, offering only the promise of a bottle and some companionship for the night. We’ll take it.

    One for the Road: While Dylan has used “All Along the Watchtower” ( shows it’s his most-played song) as a thundering closer for hundreds of performances on his Never Ending Tour, other songs from John Wesley Harding, like “Drifter’s Escape” and “The Wicked Messenger,” have joined “I’ll Be Your Baby Tonight” as semi-regular inclusions between better-known fare.

    Odds and Ends: John Wesley Harding found a very different Dylan returning to his first proper recording after his infamous motorcycle crash and sessions with The Band at Big Pink. More a collection of acoustic parables than anything else, the album is noted for its simple arrangements, economical lyrics, and Biblical qualities. Gone is the kinetic electricity and fountains of language gushing forth on previous releases, yet there’s something appealing to these simple, yet still mysterious, tales, especially when absorbed as a whole. While bands like The Beatles were pushing boundaries, Dylan — who insisted the record be released without publicity or a single — seemed to be in retreat. Regardless, the album climbed the charts in 1968 and has grown in esteem among both fans and critics ever since.

    — Matt Melis

    14. Oh Mercy (1989)

    bob dylan - oh mercy


    Runtime: 38:46, 10 tracks

    Producer: Daniel Lanois

    When I Paint My Masterpiece: The album cover comes from a bit of found art that Dylan stumbled upon — that being a mural on the wall of a Chinese restaurant in Hell’s Kitchen, Manhattan. It was a pretty damn cool photo op until painted over and replaced in 2011.

    It’s All Good: It’s debatable that until Oh Mercy, Dylan hadn’t recorded a really good song in more than half a decade. Here, there are plenty to choose from, and a lot of that credit goes to both Dylan and producer Daniel Lanois for writing and arranging songs that Dylan could embody and really wrap his voice around. “Man in the Long Black Coat” finds Dylan reciting more than singing, imbuing the lament, which could be right out of a Nathaniel Hawthorne short story collection, with an air of dark mystery and a chill that hits bone. It’s difficult to imagine both Dylan’s modern live show and his late ’90s resurgence in the studio without first mastering this type of cryptic narrative, drip-and-drab phrasing, and murky production.

    It Ain’t Me, Babe: There’s nothing egregious here that absolutely deserves the chop. While some consider “Political World” an update on “With God on Our Side,” it feels like a great groove wasted on a shrug of a message. There’s also some overlap of ideas toward the album’s end, but getting Dylan back on the songwriting horse is well worth the bits of rust here and there.


    Blowin’ in the Wind: “I can survive, and I can endure/ And I don’t even think about her/ Most of the time” — from “Most of the Time”

    This Movie I Seen One Time: Like Alvy Singer before him, Rob Gordon sabotages every relationship he’s in because he never learns to recognize a good thing when he has it. For Rob, the grass is always greener, the records minter, and the lingerie sexier in someone else’s life. However, the ultimate difference between Woody Allen’s Singer and John Cusack’s Gordon comes down to the latter hitting rock-bottom and finally understanding that he’s the one dooming his relationships by never committing. And as he sits on a bus bench in the pouring rain, breaking the fourth wall to tell us all about it, Dylan’s late ‘80s ballad “Most of the Time” drifts in like a storm cloud passing overhead. In most song-film pairings, Dylan’s music sets a tone, creates a mood, or locates a story in a time and place, but here his lyrics could be Rob’s own thoughts, desperately trying to convince himself that Laura isn’t the answer. Problem is, nobody, neither Dylan nor Rob, is buying it.

    I Threw It All Away: Dylan left a lot of gold off this record. Luckily, fan favorites like “Dignity” and “Series of Dreams” would find homes in setlists, bootlegs, live albums, and even Dylan’s official bootleg series. Either would be in the running for the album’s best song had they been included.


    One for the Road: “Man in the Long Black Coat,” “Everything Is Broken,” “What Good Am I?”, and “Shooting Star” have more or less become setlist staples over the years. “Dignity” has been in regular rotation a few times, and “Series of Dreams” remains a long shot to witness.

    Odds and Ends: Oh Mercy brings more to the table than simply not being its predecessor, Down in the Groove, or its follow-up, Under the Red Sky, though, admittedly, its lousy neighbors in the Dylan catalog certainly might bias us a bit. In his memoir, Chronicles: Volume One, Dylan surprisingly devotes an entire section (or 20% of the book) to his time spent struggling to record Oh Mercy in New Orleans with producer Daniel Lanois. To Dylan, this batch of songs, even if flawed, signified the first time in a long while that he felt himself compelled to write new material — “chasing songs,” as he puts it.

    For fans, this record has become somewhat of a grower over the years. Maybe it was watching High Fidelity’s lovelorn Rob sitting in a downpour during “Most of the Time”; gentle lament “Shooting Star” and “Man in the Long Black Coat” becoming Never Ending Tour staples; or sensing that the driving sound found on Time Out of Mind a decade later owed something to these songs, but somewhere along the line we started liking this record quite a bit. Oh, mercy, mercy me.

    — Matt Melis

    13. Modern Times (2006)

    bob dylan - modern times


    Runtime: 63:04, 10 tracks

    Producer: Jack Frost (ahem)

    When I Paint My Masterpiece: Fans of Dean Wareham’s Luna will likely recognize Modern Times’ artwork — that’s Ted Croner’s Taxi, New York at Night, which appears on the ‘90s dream pop outfit’s “Hedgehog” / “23 Minutes in Brussels” single and in the liner notes of its parent album, Penthouse. It might seem ironic at first glance for Dylan to use a photograph from 1947 as cover art for a record titled Modern Times, but then again, little of Modern Times sounds modern. Instead, the blurry, spectral image of a taxicab almost perfectly reflects both its constant motion as well as its timelessness, how it seems to phase in and out of the present moment.

    It’s All Good: Like “Love and Theft” before it, Modern Times drew accusations of plagiarism, with Dylan claiming old blues riffs as his own and swiping lines from the likes of Ovid and Henry Timrod. However, this has proven to be one of Dylan’s greatest strengths in the twilight years of his career, using these elements as building blocks for something completely new, in the same way that producers in the golden age of hip-hop constructed beats from familiar samples. “Ain’t Talkin’,” Modern Times’ bone-chilling closer, swipes lines from the traditional “The Wayfaring Stranger” and the Stanley Brothers’ “Highway of Regret,” then flips the songs’ sentiments on their head: It’s not deliverance that Dylan’s yearning for, but vengeance, vowing to slit his enemies’ throats in their beds. He’s sung about the world’s end before, but on “Ain’t Talkin’,” Dylan himself sounds apocalyptic, like he’s the last thing his wrongdoers will see before they die.

    It Ain’t Me Babe: Modern Times is at its weakest — or at least its least interesting — when its bluesy influences are the most noticeable. The musical roots of “Rollin’ and Tumblin’” and “The Levee’s Gonna Break” are apparent from their names alone, but at least on these songs Dylan sounds like he’s having fun with the prompt, coming across as more lascivious than lamenting when he rasps “some young lazy slut has charmed away my brains” on the former. By contrast, “Someday Baby” — an adaptation of Sleepy John Estes’ “Someday Baby Blues” — feels limp and indistinct.


    Blowin’ in the Wind: “You think I’m over the hill/ You think I’m past my prime/ Let me see what you got/ We can have a whoppin’ good time” — from “Spirit on the Water”

    Gone but Not Forgotten: Dylan and Merle Haggard were mutual admirers (and, in 2005, tourmates), so the title of “Workingman’s Blues #2” scans as a clear homage to Haggard’s “Workin’ Man’s Blues.” But where Hag’s hit was an ode to the integrity and the hardiness of blue-collar Americans, Dylan’s spiritual sequel is wearier, sung from the perspective of someone who knows he’s playing a game he can’t possibly win, in which the rules are constantly being rewritten by forces beyond his control. “The buying power of the proletariat’s gone down,” Dylan sings over gorgeous piano. “They say low wages are a reality/ If we want to compete abroad.” It’s one of Dylan’s most somber statements on class struggles — and one of his sharpest.

    One for the Road: Only one song from Modern Times has been played semi-regularly in concert, and that’s the rollicking “Thunder on the Mountain.” Loaded with Biblical imagery and some wickedly funny lyrics — “I’ve sucked the milk out of a thousand cows,” “I got the porkchops, she got the pie,” a “sons of bitches” / “orphanages” rhyme — it already feels as much a standard in Dylan’s catalogue as “It Ain’t Me Babe” and “Highway 61 Revisited.”


    Odds and Ends: The shout-out to Alicia Keys on “Thunder on the Mountain” caught more than a few critics by surprise, and Dylan later explained that he wrote those lines after being impressed by Keys’ performance at the Grammy Awards in 2002 (at which she won five awards, including Best New Artist and Song of the Year). But they’re actually lifted from Memphis Minnie’s “Ma Rainey,” which she wrote as a tribute to the legendary blues singer in 1940 — read its lyrics here. For her Jack White-assisted cover of “Thunder on the Mountain” in 2011, rockabilly pioneer Wanda Jackson switched out Keys’ name for “Jerry Lee” (Lewis).

    — Jacob Nierenberg

    12. Nashville Skyline (1969)

    bob dylan - nashville skyline

    Runtime: 27:14, 10 tracks

    Producer(s): Bob Johnston and Steve Berkowitz

    When I Paint My Masterpiece: Dylan looks inscrutable, or at least aloof, on many of his album covers. So it’s disarming to see him with a big grin, mid-tip of the hat, on the front of Nashville Skyline. As much as we’re looking at him, he seems to be looking back at us, and there’s a warmth to his gaze that feels all the more affecting coming from the trailblazer who once sneered, “How does it feeeel?”

    It’s All Good: Right from the jump, Nashville Skyline throws listeners a few curveballs. You’re almost taken aback to hear Dylan singing, trying on a gentle croon that at times sounds closer to Morrissey’s voice than his own. And just as that shock starts to fade, there’s another: Is that Johnny Cash singing the second verse? Dylan had outraged the folkies several years prior when he went electric, and now it looked like he was about to do the same to the rockists by going country — and he very well might have if Nashville Skyline’s opening track, “Girl from the North Country,” reimagined as a duet with the Man in Black, weren’t so damned good. “Girl from the North Country” already sounded like a traditional ballad when we first heard it on The Freewheelin’ Bob Dylan, so it only made sense to give it the country treatment. Still, the Nashville Skyline version feels like the form the song was always meant to take.


    It Ain’t Me Babe: Nashville Skyline doesn’t have any outright howlers, and even its weaker songs, like “Peggy Day” and the goofy, minute-and-a-half-long ditty “Country Pie,” are charming. “Nashville Skyline Rag” is a fun instrumental that you could play at a hoedown, but it’s an instrumental nonetheless, and one might wish Dylan had instead replaced it with another one of the Cash duets collected on The Bootleg Series Vol. 15: Travelin’ Thru.

    Blowin’ in the Wind: “His clothes are dirty but his hands are clean/ And you’re the best thing that he’s ever seen” — from “Lay Lady Lay”

    Gone but Not Forgotten: We could debate whether or not “I Threw It All Away” qualifies as a “deep cut,” seeing as it was Nashville Skyline’s lead single, but seeing as it’s spent decades in the shadow of “Lay Lady Lay,” I’m going to say it is. Dylan has always excelled at writing songs about lost love, from “Don’t Think Twice, It’s All Right” to “Most of the Time,” and “I Threw It All Away” is no exception. “No matter what you think about it/ You just won’t be able to do without it,” Dylan warns the listener of love, “Take a tip from one who’s tried.” What sets this one apart from the others is how Dylan not only owns his share of the blame, but isn’t in denial about his heartbreak. (Contrast this with the wounded, embittered version that appears on the live album Hard Rain.)


    One for the Road: There were two periods of time in which Dylan would open his shows with “To Be Alone with You,” a honky-tonk love song. He hasn’t played it since 2005, though, so here’s hoping he’ll dust it off and add it to the setlist once more. What better way to open a show than by singing “They say that nighttime is the right time/ To be with the one you love”?

    Odds and Ends: Kris Kristofferson played an important (albeit uncredited) role in the recording of “Lay Lady Lay.” The song’s distinctive percussion features a pair of bongos and a cowbell during the verses, and Kristofferson — then working as a janitor at Columbia Recording Studios — was asked to hold these instruments for percussionist Kenny Buttrey, allowing him to play the drum parts during the chorus. Buttrey moved the drum microphone directly over Kristofferson so it could pick up these sounds more clearly, which had the added effect of making his drumming sound fainter. The first take wound up becoming the master take, and Buttrey would later call it one of his favorite performances.

    — Jacob Nierenberg

    11. Another Side of Bob Dylan (1964)

    Bob Dylan - The Times They Are a-Changin

    Runtime: 50:37, 11 tracks

    Producer: Tom Wilson

    When I Paint My Masterpiece: While he’s far from cracking a smile or appearing happy-go-lucky in the Sandy Speiser photo that would become the cover art for Another Side of Bob Dylan, the songwriter’s wardrobe — more James Dean than Woody Guthrie — can be considered telling.


    It’s All Good: Pop music owes at least a third of its cannon to men professing their love for women and outlining the perilous slings and arrows they would face in order to win that lady’s favor. In actuality, there are limits to our chivalry, compromises, and willingness to change in order to accommodate love. By 1964, Dylan, much to the consternation of some listeners, had already begun drifting away from protest music and turning inward for songwriting inspiration. “It Ain’t Me Babe,” the final cut on the sea changing Another Side of Bob Dylan, further irons out a theme that Dylan introduced on “Don’t Think Twice, It’s Alright”: the desire for love but on his own terms.

    Some have read Dylan’s professions as a commentary on blind patriotism, but really it’s just a brutally honest breakup song. Dylan’s attitudes towards women are surely worthy of a slew of doctoral theses and several bulging volumes, but one characteristic we see from his earliest days is his unwillingness to wear shackles of any type — whether the irons be politics, public perception, musical genre, or love. It ain’t for him, babe.

    It Ain’t Me, Babe: Dylan himself admits that “Ballad in Plain D,” which takes plenty of liberties as it tackles his breakup with girlfriend Suze Rotolo, is a song he could’ve “left alone.” From our perspective, while it does show Dylan reaching for more personal material, it’s also an eight-minute clunker that fruitlessly dumps Dylan back in the folksong tradition with little to show for the regression other than weighing down a brilliant back half of the album.


    Blowin’ in the Wind: “It ain’t me, babe/ No, no, no, it ain’t me, babe/ It ain’t me you’re looking for, babe” — from “It Ain’t Me Babe”

    Gone but Not Forgotten: Amid such significant changes in Dylan’s direction as a songwriter, it can be easy to overlook the unassuming and tender folk waltz of “Ramona.” Yet, it’s also a beautiful early example of Dylan treating ideas of romance and non-conformity with real emotional heft and even some irony as he realizes he’ll likely be crying on Ramona’s shoulder before long with similar problems.

    One for the Road: Dylan has played seven of the album’s 11 tracks in concert, with “It Ain’t Me Babe” having been performed more than 1,000 times. “I Don’t Believe You (She Acts Like We Never Met),” “To Ramona,” and “My Back Pages” have all been regular setlist inclusions at different points. The latter was famously covered (see above) by a who’s-who of rock-and-roll royalty at Madison Square Garden in 1992 for a concert-long tribute to Dylan’s first 30 years in the recording industry.


    Odds and Ends: The gentle strum, warbling choruses, and warm harmonica on opener “All I Really Wanna Do” already suggest that times have a-changed since Dylan’s collection of protest songs dropped earlier in 1964. The cataloging song takes a sharp (but often humorous) razor to any and all motivations (“I ain’t lookin’ for you to feel like me/ See like me or be like me”) Dylan has other than to be friends. To many fans in the folk scene, it felt like an abject betrayal. Dylan biographer Clinton Heylin described it as the songwriter “pass[ing] from topical troubadour to poet of the road.”

    In either case, songs like “Chimes of Freedom,” “My Back Pages,” and “It Ain’t Me Babe” made it clear that Bob Dylan the songwriter would not be constrained by form, philosophies, or public pressure. When compared to other seismic shifts in his career, Another Side of Bob Dylan might seem like only a subtle shuffle to the side, but it’s arguably the first major step (after starting to write his own songs) towards Dylan becoming the songwriter who’d go on to reshape rock and roll in his enigmatic, ephemeral image.

    — Matt Melis

    10. “Love and Theft” (2001)

    bob dylan - love and theft

    Runtime: 57:25, 12 tracks

    Producer: Jack Frost (Bob Dylan)

    When I Paint My Masterpiece: As Dylan album covers go, this is one of the more straightforward ones. As opposed to Blonde on Blonde’s blurry, unfocused Dylan, here the image is clear, and he seems to be making a special point of looking directly at his audience. He looks like he could have come from a session at the studio, tired after the day’s work.


    It’s All Good: “High Water (For Charley Patton)” is fascinating not only as a song — and it is great in its own right — but also for the way it weaves together so many strands of history, illuminating in particular the intersecting histories of racism, displacement, and American popular music. “High Water” is a reference to Delta blues legend Charley Patton’s “High Water Everywhere,” which documented the 1927 Great Mississippi Flood, in particular in relation to systemic racism and the displacement of so many Black Americans who lost their homes. Dylan sings this song not only for Patton but for Robert Johnson, referencing his song “I Believe I’ll Dust My Broom,” as well as Big Joe Turner.

    As an artist, Dylan will be the first to admit he is no island cut off from the tapestry of American music, and his influences are front-and-center on “Love and Theft”. It’s notable that in approaching complex histories on this record, Dylan doesn’t simply paraphrase the story in his own words; rather, he lets the stories of others show through the cracks in his song, interweaving their voices with his.

    It Ain’t Me Babe: “Honest with Me” comes off a bit jarring sandwiched between the Shadows in the Night-esque “Moonlight” and “Po’ Boy,” and, although it is a dynamic track, it feels slightly out of place in the context of the album’s sequencing.


    Blowin’ in the Wind: “All my powers of expression and thoughts so sublime/ Could never do you justice in reason or rhyme” — from “Mississippi”

    Gone but Not Forgotten: “Moonlight” is perhaps easy to overlook — it sounds like a classic ballad and strikes a sentimental tone, and it’s not as immediately captivating as standouts like “Mississippi” and “High Water.” However, its beauty is undeniable, and there’s something touching about its simplicity. According to the sound engineer Chris Shaw, who discussed the song with Uncut, the recorded version is only the second take, recorded live, no overdubs or edits: “It all just flowed together at once, and it was a really beautiful moment.” You can hear something oduf the natural, extemporaneous quality of the recording in the finished product.

    One for the Road: A welcome fast-paced, rockabilly-influenced number, “Summer Days” finds Dylan leaning into the influence of Buddy Holly and Chuck Berry. It genuinely sounds like Dylan’s having loads of fun, and the energy is infectious. It’s no wonder that it became the most-played song from “Love and Theft” on Dylan’s Never Ending Tour.


    Odds and Ends: For most artists, following up an album like Time out of Mind would be paralyzing, but Dylan’s ambivalence to his audience’s expectations has often worked out in his favor. “Love and Theft” marks the second entry in a string of late-career masterpieces, bookended by careful studies of traditional folk and pop standards, respectively, with albums like Good as I Been to You and Shadows in the Night. Dylan’s careful attention to and study of history and his own musical roots is especially prevalent on “Love and Theft” and Modern Times especially. It is in large part Dylan’s intimate awareness of the interconnectedness of history that makes these albums special.

    Tyler Dunston

    09. Desire (1976)

    Bob Dylan - Desire

    Runtime: 56:13, 9 tracks

    Producer: Don DeVito

    When I Paint My Masterpiece: The cover portrait of Dylan in profile seems to evoke the album of sympathetic outlaw tales to follow. Against a blurry green-treed background, he wears a banded western hat, fur-hooded coat, and fluttering silk scarf – and seems to be in motion and…smiling? Perhaps unintentionally, the image is very similar to the cover of John Phillips’ 1970 album, John Phillips (John, the Wolf King of L.A.)

    It’s All Good: “Hurricane” and “Isis,” the first two songs on record, are both lengthy story songs — two of Dylan’s most cohesive — co-written with Jacques Levy. Perhaps Dylan’s most propulsive “topical” track, “Hurricane” gives account of the false murder conviction of boxer Rubin Carter, and it’s a rollicking musical ride. On the other hand, “Isis” is nearly a waltz, built around sweetly swinging violin and low-rumbling piano. The fable follows a young groom’s quest for foolhardy adventure and his return to an enigmatic love, touching on Desire’s recurring theme of marriage.


    It Ain’t Me Babe: Go ahead and skip “Joey,” a long-winded image- softening of mafioso Joey Gallo. In 2009, Dylan claimed that Levy wrong the controversial lyrics to the song, and he only sang them.

    Blowin’ in the Wind: “Put him in a prison cell, but one time he could-a been the champion of the world” — from “Hurricane”

    “She said, ‘You been gone’; I said, ‘It’s only natural’/ She said, ‘You gonna stay?’; I said, ‘If you want me to, yes’” — from “Isis”


    Gone but Not Forgotten: “One More Cup of Coffee” embodies the mystical, feminine, collaborative quality that defines Desire. This ode highlights the vocals of Emmylou Harris and mournful violin of Scarlet Rivera. Their influences seem to push Dylan to stretch his vocal interpretation as he warbles for a self-possessed lover beyond his reach.

    One for the Road: “Oh Sister” is another duet with Harris, woven with Rivera’s fragile, insistent strings. The down-tempo dialogue on how love can last is awash in echoing drums and harmonica, and became a live show favorite of this era.

    Odds and Ends: Though the recording process of Desire was reportedly chaotic, it illustrates Dylan’s pursuit of full-band collaboration — and features the artistic influence of women in a major way. While Blood on the Tracks is often viewed as Dylan’s account of his disintegrating marriage with Sara Lownds, most of the standout songs on Desire seem to show the musician grasping at the last bright threads of their relationship. Sara was reportedly visiting the studio when he recorded “Sara,” one of his most baldly personal compositions, a plea for a blaze already slipped below the horizon.

    Katie Moulton

    08. The Basement Tapes (1975)

    bob dylan - the basement tapes


    Runtime: 76:41, 24 tracks

    Producer: Bob Dylan and The Band

    When I Paint My Masterpiece: Photographer Reid Miles took the cover art photo in the basement of a Los Angeles YMCA, with those present dressing as characters alluded to in songs from the sessions. Credit Miles with absolutely capturing the joy, camaraderie, and goofiness of these sessions and proving once and for all that it is indeed fun to stay at the YMCA.

    Lo and Behold!: In 1966, Dylan, then at the height of his popularity and creative powers, survived a dangerous motorcycle accident that left him with several broken vertebrae. He holed up the following year in rural eastern New York and invited members of his touring band, The Hawks, who within a year’s time would begin their ascent into the rock and roll pantheon as The Band, to record demos with him. The sessions yielded rough recordings of well over 100 original songs, covers, and sketches, several of which subsequently became hits for The Band and popular contemporary acts like The Byrds, Manfred Mann, and Peter, Paul and Mary. As curiosity about these sessions germinated, bootleg recordings soon began to surface (most notably 1969’s Great White Wonder), which sparked demand for the eventual official release of beloved 1975 sampler The Basement Tapes.

    It’s All Good: While it’s far better known as Richard Manual’s soulful opener on The Band’s Music from Big Pink, Dylan more than holds his own in this version. In fact, for my money, the restored version on The Basement Tapes Complete trumps all others, Dylan’s aching, fatherly voice intertwined with Manuel’s (daughterly?) falsetto to render the parental pain all the more palpable in this song about a declining, wayward America.


    It Ain’t Me, Babe: You’re missing the spirit of this thing, mate.

    Blowin’ in the Wind: “Look here you bunch of basement noise” — from an early version of “You Ain’t Goin’ Nowhere”

    Gone but Not Forgotten: The Basement Tapes sessions came at the outset of a new era for Dylan — a time when he would stop touring, remain largely secluded from the public eye, and attempt to cut virtually all ties with his career and persona from before the motorcycle accident. On the song “Goin’ to Acapulco,” a world-weary protagonist plans on “goin’ on the run” to a place where he is finally “goin’ to have some fun.” Judging by the original Basement Tapes and sessions made available later, Dylan found his Acapulco with four Canadians in the basement of a pink house in rural New York. It’s not Mexico, but close enough.

    One for the Road: While these songs were bigger hits for The Band and other artists than they ever were for Dylan, that didn’t stop them from working their way into his setlists over the years. “Tears of Rage,” “This Wheel’s on Fire,” “You Ain’t Goin’ Nowhere,” “Crash on the Levee,” and others, in one form or another, found their way into concerts — in some cases as staples for a time.


    Odds and Ends: Nearly 50 years later, these sessions still capture public imagination as a rare glimpse of Dylan during both a personal and career sea change; a peek at one of the most talented and eclectic bands in rock history on the verge of breaking out on their own; and, in some eyes, the progenitor of both the Americana genre and the modern bootleg. In short, for many, The Basement Tapes sessions are the Dylan holy grail. And that’s fair. While this sampler of brilliant performances and pure curiosities may in some ways fail as the album it never was intended to be, it absolutely documents and sheds light on rock and roll history while totally sparking the imagination. That’ll do.

    — Matt Melis

    07. Time Out of Mind (1997)


    Runtime: 72:50, 11 tracks

    Producer: Daniel Lanois

    When I Paint My Masterpiece: The black-and-white album cover was shot in the studio by Daniel Lanois. Given the manner in which Dylan and the producer have tended to butt heads on projects, including Time Out of Mind, one might argue this blurry photo represents the pair’s inability to entirely agree on a vision. Luckily, their differing vantages have yielded two entries on this list. It seems that iron sharpens cold irons.

    It’s All Good: Not many artists are reborn at 55. By that time, a songwriter generally sticks to treading the terrain he staked out for himself long ago. But on Time Out of Mind, Dylan, who hadn’t released a record of new material in seven years, blew past old boundaries like a Depression-era bank robber racing for the county line. It’s an agitated, pining, and paranoid album, and nowhere do those emotions register more tangible than on “Cold Irons Bound.”


    Amid driving percussion and echoing dirt-road blues, Dylan fails to square a love and obsession that just can’t be reasoned with. This isn’t a tearful goodbye and gallop off into the sunset; this is a collision course that a desperate and broken man seems powerless to avoid. Like so much of Dylan’s turn-of-the-century work, there’s zero compromise to be found here. The wounds are deep, the pain is unbearable, and any possible consolation is blowin’ in the wind.

    It Ain’t Me, Babe: It’s not that Dylan fails to conjure the sweetness he was going for on devoted ditty “Make You Feel My Love.” It’s a lovely ballad beautifully delivered and since covered by Billy Joel, Garth Brooks, Bryan Ferry, and Adele. It’s just that Dylan offers such a steady and calm shoulder here on an album where the singer routinely appears agitated, paranoid, and, in his own words: “waist deep in the mist/ It’s almost like I don’t even exist.” Then again, that’s exactly why some would argue the record needs this lush, late-album change of perception. Truth be told, we can live with it, too.

    Blowin’ in the Wind: “One look at you and I’m out of control/ Like the universe has swallowed me whole” — from “Cold Irons Bound”


    Gone but Not Forgotten: Buried between ballad “Make You Feel My Love” and epic, meandering closer “Highlands,” it’s easy to lose track of a more subtle track like “Can’t Wait.” But it’s also a perfect distillation of the obsessive, swampy dirt-road blues that Dylan and Lanois do so well together. The tune inches along like a slowly drawn blade but makes it abundantly clear that the situation is quickly turning grim as things fall apart for the song’s protagonist.

    I Threw It All Away: “Love and Theft” standout “Mississippi” was originally written for these sessions but would be abandoned only to have Sheryl Crow find success with it as well as Dylan’s next producer, Jack Frost (wink, wink). Other promising takes like “Dreamin’ of You” and “Marching to the City” would lend lyrics and evolve into “Standing in the Doorway” and “‘Til I Fell in Love with You,” respectively. All of these early stabs can be heard on Tell Tale Signs from The Bootleg Series, including shelved standout “Red River Shore.”

    One for the Road: Here’s a pretty good indicator of how relevant this album remains to Dylan’s live show. In his last concert before COVID-19 put a halt to live music for the foreseeable future, Dylan drew four songs (“Can’t Wait,” “Make You Feel My Love,” “Not Dark Yet” and “Tryin’ to Get to Heaven”) from Time Out of Mind — more than any other record.


    Odds and Ends: I’ve always assumed the PSA that commences every Bob Dylan show and details, among other things, Dylan’s battles with substance abuse and subsequent finding of Jesus must have been penned by the songwriter himself with tongue firmly planted in cheek. About the only part of the intro that seems genuine is the line that says, “written off as a has-been … before releasing some of the strongest music of his career beginning in the late ‘90s.” Now, that seems pretty much spot-on. You arguably have to go back in Dylan’s catalog to the ‘60s triumvirate of Bringing It All Back Home, Highway 61 Revisited, and Blonde on Blonde to find a stronger three-album run than Time Out of Mind, “Love and Theft”, and Modern Times.

    Reunited with the swampy blues production of Daniel Lanois, Time Out of Mind finds Dylan teetering on the emotional brink (“Love Sick”), conjuring both tenderness and enmity for an ex-lover (“Standing in the Doorway”), and violently brooding on the outskirts of town (“Cold Irons Bound”). It’s a dark, primal, and troubled album, with stakes that seem a million times higher than when Dylan was merely trying to save his soul, and ours, for Jesus. After more than a decade of forgettable, boring records, Time Out of Mind opened a floodgate of creativity that’s made it impossible to ignore Dylan’s work ever since.

    — Matt Melis

    06. The Times They Are a-Changin’ (1964)

    Bob Dylan - The Times They Are a-Changin

    Runtime: 45:36, 10 tracks

    Producer: Tom Wilson

    When I Paint My Masterpiece: The photo of a serious Dylan looking uneasy was snapped by photographer Barry Feinstein on the balcony of a friend’s New York City penthouse. It’s been remarked that the expression on Dylan’s face matches the album’s tone and notable lack of humor.


    It’s All Good: Dylan makes no bones about “The Times They Are a-Changin’” having been written with a very specific purpose in mind. “I wanted to write a big song, with short concise verses that piled up on each other in a hypnotic way,” he once told Cameron Crowe. “The civil rights movement and the folk music movement were pretty close for a while and allied together at that time.” Nearly 60 years later, it’s arguably Dylan’s pre-“Like a Rolling Stone” calling card and as important and fine a song as he’s ever composed. Like so many of Dylan’s most famous “protest” songs, its message and pleas to young people, parents, the media, and politicians resonate as strongly as ever today.

    Great songs touch upon some truth, and that’s why they remain timeless. No matter how politics, technology, or society evolve, some ideas prove eternal for us. Dylan set out to create an anthem of change for his generation, and “The Times They Are a-Changin’” became much more than that. Not only do its general lyrics make it a timeless call to action, but it also speaks to ideas of inevitable justice and the need for each generation to understand both its purpose and duty to step down once that purpose has been served. In that sense, it’s always been a baton song of sorts. One that asks you to play your part and then let others step in and play theirs, hopefully having eased that next generation’s path a bit.

    Not sure of this song’s relevance? Think of any social injustice that still plagues our society, and then consider all the “writers and critics,” the “senators and congressman,” and all the “mothers and fathers throughout the land” who don’t “lend a hand” but instead actively oppose positive change. As hatred, bigotry, and superstition continue to rear their ugly heads, we can only hope that humanity chooses to swim rather than sink like stones.


    It Ain’t Me, Babe: Perhaps a precursor to “Idiot Wind” a decade later, closer “Restless Farewell” deals in part with the media and opposition Dylan had met in his short time in the spotlight. While out of place on an album of no-nonsense protest songs and more traditional folk fare, Dylan’s turn inward can also be seen as one of the first of several recorded goodbyes (or good riddances) to the world of protest music. But what a lyric to go out on: “So I’ll make my stand/ And remain as I am/ And bid farewell and not give a damn.”

    Blowin’ in the Wind: “The battle outside ragin’/ Will soon shake your windows and rattle your walls/ For the times they are a-changin'” — from “The Times They Are a-Changin’”

    Gone but Not Forgotten: Most of Dylan’s great “protest” songs are timeless because they speak in simple and broad terms about problems that sadly still exist in our society more than a half-century later. However, “The Lonesome Death of Hattie Carroll” draws upon a particular news story of a Black domestic being murdered by her wealthy, young, white employer in a fit of rage. Dylan’s phrasing circles around the subsequent trial like a bald eagle searching for justice, only to find bitter tears when the murderer receives a slap on the wrist. Sadly, this based-on-a-true-story look at racial injustice feels painfully relevant in 2021 as protests and calls for police reform sweep our nation.


    But we also can’t forget about…

    The ballad “Boots of Spanish Leather” unfurls as a dialogue between two lovers, a woman setting sail for a trip overseas and a man remaining behind. The first six verses find her asking him what he might like her to send him as a souvenir, to which he continually insists that her safe return would be enough. Her suggestion that she might be gone for a long time, along with a letter she sends him, which he reads and replies to in the final three verses, makes it clear to him that their love is over and that the gift is at worst a sort of buy-out to ease her guilt and at best a token to remember her by.

    Dylan, not known for his narratives, brilliantly shows the unraveling of the relationship in verse, especially the final words the man sends: “So take heed, take heed of the western winds/ Take heed of the stormy weather/ And yes, there’s something you can send back to me/ Spanish boots of Spanish leather.” We find his earlier poetic, romantic sentiments replaced by pleasantries and an order for one pair of Spanish boots. It’s a simple, yet heartbreaking tale showing Dylan as a master of a common folktale trope.

    This Movie I Seen One Time: Whether or not you approve of Zack Snyder’s silver-screen adaptation of Alan Moore and Dave Gibbons’ iconic mid-‘80s comic-book series Watchmen, the combination of this record’s titular anthem and the film’s opening images showing how an alternative history led to a particularly terrifying state of world affairs can’t help but “shake your windows and rattle your walls.”


    One for the Road: Dylan has continued to play the title track live throughout his career, his cadences more gentle than blunt in recent years. “Hattie Carroll” and “Boots of Spanish Leather,” a gem that often brings out Dylan’s finest vocals, have also remained setlist mainstays.

    Odds and Ends: Like its title track, Dylan’s first of two 1964 albums – noted for its straightforwardness, sociopolitical content, and lack of humor – seems to be equally on a mission. With that initial “Come gather ‘round people,” Dylan ushers in listeners to hear grim tales of racial injustice (“The Lonesome Death of Hattie Carroll”), colorblind poverty (“Only a Pawn in Their Game”), God-fearing nationalism (“With God on Our Side”), and workers wronged (“North Country Blues”). It’s Dylan at his most transparent but also proving how stirring he could be with just a simple strum and a message. Though later the same year he would leave protest songs behind for good, the sentiments found in the songs of The Times They Are a-Changin’ remain timeless a half-century later.

    — Matt Melis

    05. Bringing It All Back Home (1965)

    Bob Dylan - Bringing It All Back Home

    Runtime: 47:21, 11 tracks

    Producer: Tom Wilson

    When I Paint My Masterpiece: This cover is filled with easter eggs — albums by Robert Johnson, Ravi Shankar, and Dylan himself (you can just see the top half of Another Side of Bob Dylan in the background), some Beat poetry, a copy of Time magazine, etc. etc. But the real star of the show is the adorable gray kitten in Dylan’s arms.


    It’s All Good: Yes, The Byrds propelled the song to fame, but they also cut out some of the best verses. Dylan’s version of “Mr. Tambourine Man” remains one of his best songs, with surreal, Rimbaudian lyrics dripping with sorrow for all their idealistic imagining. The disconnect between wish and reality — “My ancient empty street’s too dead for dreaming,” “Let me forget about today until tomorrow” — lends the song a weight which tethers it to earth even as its speaker looks skyward.

    It Ain’t Me Babe: Lyrically, “On the Road Again” is peak satirical Dylan, but musically it’s pretty straightforward — Dylan sounds great as always playing the 12-bar blues, but it feels more like a vehicle for his words here than an inevitability. Especially on an album where questions of instrumentation and composition carry such weight — this is the record where Dylan first went electric, split in two between acoustic and electric sides — this song feels less considered.

    Blowin’ in the Wind: “Yes, to dance beneath the diamond sky with one hand waving free/ Silhouetted by the sea, circled by the circus sands/ With all memory and fate driven deep beneath the waves/ Let me forget about today until tomorrow” — from “Mr. Tambourine Man”


    Gone but Not Forgotten: The William Blake-inspired false paradise depicted in “Gates of Eden,” like many of the songs on this record, shows the extent to which Dylan had become less direct and more obfuscating lyrically. Like Blake, Dylan’s juxtaposition of innocence and experience is one in which the two are aesthetically emphasized by the presence of their opposite. Mirroring Dylan’s alienation of his fans when he turned electric, this song also represents a turning away from Dylan’s more idealistic work on previous records (it is a far cry even from “Mr. Tambourine Man,” which immediately precedes it). Futility permeates this image of paradise. “All and all can only fall/ With a crashing but meaningless blow.”

    One for the Road: Bob Dylan never performed “Outlaw Blues” until 2007, but when he did, it was a memorable affair, as he played it alongside Jack White of The White Stripes, who sang and played guitar with Dylan onstage, at the Ryman Auditorium.

    Odds and Ends: Bringing It All Back home will always be described as transitional, an incredibly polarizing record which alienated Dylan’s folk base but also notably gave him his first top 10 record in the U.S. and his first charting single (“Subterranean Homesick Blues”). Nevertheless, Bringing It All Back home deserves a place among Dylan’s best records, as well as one of his most varied sonically and thematically. And as a transitional record, it provides a fascinating glimpse into Dylan in the process of self-discovery and reinvention.

    Tyler Dunston

    04. The Freewheelin’ Bob Dylan (1963)

    Bob Dylan - The Freewheelin' Bob Dylan


    Runtime: 50:04, 13 tracks

    Producer(s): John Hammond and Tom Wilson

    When I Paint My Masterpiece: CBS photographer Don Hunstein snapped this photo of a freezing Dylan and bundled-up girlfriend Suze Rotolo. The iconic cover has been parodied and replicated (watch Vanilla Sky) many times, but its main legacy is that it helped to usher in an era where album artwork looked less posed and more natural.

    It’s All Good: Trying to pick the best song from Freewheelin’ is a daunting task, not only because it’s chock-full of timeless, life-altering songs, but because nearly every song on the record seems to know something essential about either the private or public lives of Americans (and many other peoples). A song like “Blowin’ in the Wind,” for instance, says as much today about the George Floyd murder as it did during the American civil rights movement. The vitriol of “Masters of War” and portent of “A Hard Rain’s A-Gonna Fall” couldn’t be more relevant if Dylan had written these songs in 2021. That said, we’ll side with “Blowin’ in the Wind” while understanding that so many of these songs have etched their words into our hearts and continue to reflect our souls and hopes for a better tomorrow.

    Most people’s relationship with Dylan the songwriter begins with “Blowin’ in the Wind.” Dylan claims to have written it in 10 minutes, and his spare strumming and steady delivery sound simple enough to have actually hitched a ride on the wind itself, but the song’s impact has been profound and lasting. For many, it introduced the modern idea of the protest song and became the anthem of the civil rights movement in America. Upon first hearing the song, Mavis Staples recalls being shocked that a young white man could express the plight of African Americans so acutely. King of Soul Sam Cooke not only took to performing Dylan’s song but responded with his own anthem, “A Change Is Gonna Come.” And the tune remains as relevant as ever as we sadly address many of the same questions Dylan posed more than half a century ago. However, the most important, and perhaps damning, question still remains: When Dylan assures us that the “answer is blowin’ in the wind,” does that mean it’s so simple that it’s staring us right in the face, or are we doomed to forever chase the solution like an elusive feather riding a relentless gust?


    It Ain’t Me, Babe: Given the gravity (not a word Dylan would use) of so many of these songs, the spastic blues of “Honey, Just Allow Me One More Chance” seems slight and a pointless cover. The comical closing rewrite of Led Belly’s “We Shall Be Free” also feels like a tacked-on song that brings one of the great albums of all time to an anticlimactic ending. Shame.

    Blowin’ in the Wind: “The answer, my friend/ Is blowin’ in the wind/ The answer is blowin’ in the wind.” — from “Blowin’ in the Wind”

    Gone but Not Forgotten: Among all the powerful social commentary and topical talkin’ blues comes the sweet cover of “Corrina, Corrina”, a pining song every bit as lovely as the far more celebrated “Girl from the North Country”. It also has a gallop that sets it apart from its surrounding tracks and hints at the type of blues Dylan would dig into on less topical albums to come.


    One for the Road: Dylan returns to the album’s most celebrated songs on the regular. Part of the appeal over the years has been seeing how he puts different spins on songs that once only featured him, a guitar, and a mouth harp. He’s turned “Blowin’ in the Wind” into a duet with the likes of Joan Baez, roared through “A Hard Rain’s…” as an apocalyptic jam, and playfully toyed with the tempo and nasally phrasing of “Don’t Think Twice” several times. Regular attendees of his Never Ending Tour can attest that it’s often not what Dylan plays, but how he chooses to play it that keeps them guessing and coming back.

    Odds and Ends: Songs were coming fast and furious by the time Dylan set out to record The Freewheelin’ Bob Dylan (original titled Bob Dylan’s Blues); so rapid and fruitful was the evolution of Dylan’s songwriting that new pieces were being recorded to replace tracks that had just been cut in previous sessions. Some attribute this wellspring of inspiration to the circles Dylan was now moving in or to his travels abroad; regardless, during this time, Dylan penned songs that would both capture the imagination of a generation and find a permanent home in the American songbook.

    By applying broad, anthemic lyrics to traditional folk melodies, these songs have become timeless commentaries on themes of equality (“Blowin’ in the Wind”), the military-industrial complex (“Masters of War”), social justice (“A Hard Rain’s A-Gonna Fall”), and even romantic farewells (“Don’t Think Twice, It’s All Right”). It’s these compositions — and those to follow on The Times They Are a-Changin’ — that, much to his chagrin, would cause millions to look to Dylan as not only a songwriter, but the “Voice of a Generation.”

    — Matt Melis

    03. Highway 61 Revisited (1965)

    Bob Dylan - Highway 61 Revisited


    Runtime: 51:26, 9 tracks

    Producer(s): Bob Johnston and Tom Wilson

    When I Paint My Masterpiece: “What are you gonna do about it, buster?” That’s how photographer Daniel Kramer described Bob Dylan’s hostile, moody gaze on the cover of Highway 61 Revisited. The white-bordered photo features Dylan sitting on a stoop, holding his Ray-Ban sunglasses in his right hand, head cocked in a direct scowl. In contrast with Kramer’s Grammy-nominated cover for Bringing It All Back Home, this image appears mostly clean of symbolism and pop-culture ephemera. However, Dylan wears a T-shirt emblazoned with a Triumph motorcycle; within a year he will crash that same vehicle and enter yet another period of transformation.

    It’s All Good: The album begins with a door kicked open, a carnival piano and Al Kooper’s stowaway organ shambling through, and Dylan punching the words “Once upon a time” with an accusing sneer. On an album stacked with compelling tracks, “Like a Rolling Stone” is legendary for good reason. It’s simultaneously the definition of and rebuke of a generation.

    It Ain’t Me Babe: “From a Buick 6” is a straight-ahead blues groove with macabre themes and lyrics borrowed from Sleepy John Estes’ 1930 song “Milk Cow Blues.” Mike Bloomfield’s guitar laces traditional riffs with his own off-kilter ideas, and Kooper gets unhinged on the organ. The shortest track on album sounds like a dark lark, referencing the heroes of country blues who lived along the actual Highway 61. But this (honestly, great) song receives this designation here because it doesn’t feature Dylan’s thrilling world-building.


    Blowin’ in the Wind: “God said to Abraham, ‘Kill me a son,’/ Abe said, ‘Man, you must be puttin’ me on’/ God say, ‘No’/ Abe say, ‘What?’/ God say, ‘You can do what you want, Abe, but/ The next time you see me comin’ you better run’” – “Highway 61 Revisited”

    Gone but Not Forgotten: “Ballad of a Thin Man” can’t be called a deep cut, but it stands out here as a track that has persisted in Dylan’s catalog and live shows. Its eerie blues and the character of “Mr. Jones” sound like they exist beyond era, beyond cultural-musical moment, and beyond Dylan himself.

    One for the Road: “Desolation Row,” the only non-electrified track on the album, is an 11-minute-plus purgatorial opus. The song has inspired many worthwhile alt-takes and memorable live performances, including from Dylan’s contentious show at Royal Albert Hall in 1966, which unfurls different lyrics than the album recording, spinning anxiously through a seemingly endless corridor of surreal vignettes.


    Odds and Ends: According to Dylan, Highway 61 Revisited is named for America’s historic main thoroughfare of the country blues, and his lyrics are absurd folk tales crowded with ghosts and askew archetypes, from biblical Abraham to Cinderella as Bette Davis to Einstein disguised as Robin Hood. Well-reviewed even by poet Philip Larkin, this gimlet-eyed fever dream marks Dylan’ official escape from expectation-heavy folkie youth to a rock-and- roller on his own visionary trip.

    Katie Moulton

    02. Blood on the Tracks (1975)

    Bob Dylan's Blood On The Tracks

    Runtime: 51:42, 10 tracks

    Producer: Bob Dylan

    When I Paint My Masterpiece: The portrait of Dylan on the cover of Blood on the Tracks is a perfect counterpart to the story told by its songs. It’s actually a photograph, though it doesn’t look like it, snapped mid-concert by Paul Till in 1974 and manipulated in the darkroom until it came to resemble a pointillist painting. It’s as if Blood on the Tracks’ cover, like the ten songs therein, tries to obscure the truth — stand too close to it and you might only see a bunch of dots and details — but when you take it all in it’s plain for us to see: this is Bob Dylan. And it looks like he’s in pain.

    It’s All Good: Ever since its songs were laid to tape, Dylan has denied that Blood on the Tracks was autobiographical. (Most infamously, he claimed in his memoir that it was inspired by Anton Chekhov’s short stories.) And for most of these songs, we can give Dylan the benefit of the doubt. But there’s something about “Idiot Wind” that feels too anguished and unguarded to believe that it was about anyone but Robert Allen Zimmerman. There are lines that take aim at the public and the press, who’ve deified him for so long that they’ve forgotten how to talk to him, and yet they can’t stop peddling bullshit stories about him.


    The most vicious lyrics on “Idiot Wind” appear to be directed at Dylan’s wife, from whom he’d soon separate — “I can’t remember your face anymore, your mouth has changed, your eyes don’t look into mine,” he snarls at one point — but in the song’s final verses, he turns his anger inward, implicating himself in his own downfall: “You’re an idiot, babe” becomes “We’re idiots, babe.” You shouldn’t have to suffer for your art. But you can’t fake the pain at the core of “Idiot Wind.” It blows in that bitter breeze, and by the time you feel it yourself, it’s already torn a hole through you.

    It Ain’t Me Babe: Blood on the Tracks’ lovesick spell is broken by “Lily, Rosemary and the Jack of Hearts,” a bouncy, vaudevillian yarn that feels much closer to a Steven Soderbergh screenplay than a Bob Dylan song. It’s not bad, per se — it’s just a poor fit on an album that’s otherwise (ostensibly) about the disintegration of its creator’s marriage. Remove it from the track listing and the nine songs that surround it become that much more cohesive.

    Blowin’ in the Wind: “I like your smile/ And your fingertips/ I like the way that you move your hips/ I like the cool way you look at me/ Everything about you is bringing me/ Misery” — from “Buckets of Rain”


    Gone but Not Forgotten: While the title of “You’re a Big Girl Now” looks like it might invite accusations of being sexist, it’s clear when you read the lyrics that the “big girl” Dylan is singing to is a bigger person than he is. She’s the one who’s “on dry land,” who’s already started making a new life for herself while Dylan’s out in the rain, sobbing through a closed door about how he can change if she’d only take him back. But the definitive version of the song isn’t the one on Blood on the Tracks — it’s the one that was originally slated for the album, which has since been released on both the Biograph box set and the deluxe edition of The Bootleg Series Vol. 14: More Blood, More Tracks, with its faintly glowing organ and weeping steel guitar, that stands as one of the most heartbreaking performances Dylan’s ever laid to tape.

    One for the Road: “Tangled Up in Blue” is among Dylan’s most beloved and frequently performed songs — it’s a clear highlight whenever he brings it out, and many times over the years he’s sung it with altered lyrics, switching up the pronouns and adding new verses. (His rendition on 1984’s Real Live is particularly noteworthy.) However, he retired the song from his setlists in 2019, instead electing to sing the mellower “Simple Twist of Fate.” Maybe Dylan will pick it out again when it’s safe for him to resume his Never Ending Tour.

    Odds and Ends: Blood on the Tracks was almost released in a dramatically different form. Dylan initially recorded these 10 songs over four days in New York City, and there’s an intimacy — at times, almost a crudity — to these takes that rivals even Neil Young’s Tonight’s the Night. (There are moments where you can actually hear the buttons on Dylan’s sleeves scraping against the body of his guitar.) But after his brother expressed concerns that the album sounded too stark — and possibly sensing that his lyrics were too revealing — Dylan impulsively delayed its release and re-recorded half of its tracks with local musicians in Minneapolis.

    — Jacob Nierenberg

    01. Blonde on Blonde (1966)

    Bob Dylan - Blonde on Blonde


    Runtime: 72:57, 14 tracks

    Producer: Bob Johnston

    When I Paint My Masterpiece: Much has been made of the fact that the iconic blurriness of the cover art for Blonde on Blonde was due to the fact that it was freezing cold out and photographer Jerry Schatzberg’s hands were shaking. However, though the shot itself was an accident, the choice of making it the cover art was intentional. It’s illuminating to take a look at the other photos from the same photoshoot — in most of them, the image is clear, and Dylan is looking directly at the camera. He never looks very happy to be there, though in one picture, there is the faint hint of a smile. It’s telling, then, that Dylan chose the picture that was most obfuscating. As if the blur weren’t enough, it seems as if Dylan wasn’t quite ready for the picture — or, at least, as if his mind was elsewhere. He’s looking just past the camera, as if he’s looking inward rather than outward. It’s the perfect album cover for an artist who has consistently refused to be pinned down.

    It’s All Good: This embarrassment of riches is a whirlwind of warring elements that goes down smooth for all its restlessness. If we must pick a standout, we might as well go with “Visions of Johanna,” one of Dylan’s best songs, written, it’s said, during a blackout in 1965. Lyrically, it’s one of his finest works. The animate atmosphere of the coughing pipes and the trick-playing night recalls modernists like T.S. Eliot and the howling ghost of electricity recalls Beats like Allen Ginsberg. Much more than the sum of its influences, however, “Visions of Johanna” provides some of the best examples of Dylan’s inscrutable lyrics which hit the listener emotionally before any sense can be made of them.

    In the final verse, the rhymes of showed/corrode/flowed/road/owed/loads/explodes pile on to the point where they become overwhelming, alongside a surprising succession of images and ideas — from the ambiguous abstraction of returning what was owed to the concreteness of a fish truck being loaded to the return to the speaker in the startling “while my conscience explodes.” Like the speaker, we’re about ready to burst when we arrive at the denouement of the closing couplet.


    It Ain’t Me Babe: Truly, there isn’t a bad track on this record, but if there must be one, it’s “Obviously Five Believers.” An excellent song, but it stands out a bit less brightly among its fellows on the back half of the record, especially given the fact that it is followed by the eleven-minute closing behemoth “Sad-Eyed Lady of the Lowlands,” which admittedly steals the show.

    Blowin’ in the Wind: “But when we meet again, introduced as friends/ Please don’t let on that you knew me when/ I was hungry and it was your world” – from “Just Like a Woman”

    Gone but Not Forgotten: The songs on Side 3 tend to be overlooked, but “Temporary Like Achilles,” should not be skipped. Hargus “Pig” Robbins’s piano, alongside Dylan’s mournful harmonica and moaning vocals, takes the standard spurned lover motif and makes it something uniquely affecting. The reference to Achilles, mortal for all his strength, is telling. The song’s narrator is both fascinated by his rival Achilles and struck by the hollowness of his strength, perhaps even the hollowness of his own situation.


    One for the Road: A lively, rollicking version of the stellar “Stuck Inside of Mobile with the Memphis Blues Again” appears on the Rolling Thunder Revue live album Hard Rain. It’s always good to have more recordings of this stellar track, and, although Dylan’s played this song live over 700 times, according to the Bob Dylan website, the last time he did so was in 2010.

    Odds and Ends: Blonde on Blonde really is the whole package. Lyrical brilliance, electric recordings, and that “thin wild mercury sound.” Part of what makes the record so enduring is the fact that, for all the album’s melancholy themes, the music is positively joyful. Front-to-back, it’s a joy to listen to, filled with restless energy and longing. Like many of Dylan’s greatest records, it’s an album that has appealed to casual fans and literary critics alike, as challenging and allusive as it is immediate and accessible.

    Tyler Dunston


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