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Ranking: Every Bob Dylan Album From Worst to Best

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This feature originally appeared in 2014. It’s been updated to include Bob Dylan’s new release, Triplicate. 

“The poet could not speak of himself, but only of the gradations leading toward him and away.” –Mark Strand, Sargeantville Notebook

Bob Dylan’s work will never be done. One day, the artist’s body will fail, but his work will live on. Held aloft by “mourning tongues” and woven into the very text of society itself, Dylan’s words and melodies will never cease to expand, reorder, restructure, and shift in estimation and purpose.

Dylan is perhaps the most restless of all artists. At every stage of his career, he transcended genre, redefined his medium, and grew bored, oftentimes disappearing from the public eye before emerging as someone else entirely (but always with those knowing, mischievous, and gleaming eyes). Tracking his growth over the course of more than 50 years and 37 albums (not to mention the endless bootlegs, live recordings, and reissues), we see an artist who cannot be satisfied. Endlessly self-critical, he slipped in and out of personae with the ease of a well-worn leather jacket. From Folk Savior, to Rock Agitator, to Country Buffoon, to Rock God, to Evangelical Christian, to Born-Again Jew, to Grand Statesman. Dylan has never stood still for long, and even in this 70s, he shows no sign of slowing down.

(Album Review: Bob Dylan – Fallen Angels)

Dylan’s songs are an ever-shifting tapestry of incalculable depth. His references range wildly, from the literary to the political to the personal, but remain most deeply in conversation with themselves. Each new song sets off a reverse domino effect, reaching back into the past and redefining, whether subtly or overtly, what we thought we knew. Dylan played endlessly with the mythology of himself, and of his music, leaving behind bread crumbs, frayed knots. Separating the former from the latter is one of the great pleasures of “Dylanology.”

Every new Dylan release is an opportunity to check in with the grand master and track his progress across our shared cultural imagination. To honor this endless, shifting legacy, we’ve attempted to rank and reorder Dylan’s studio albums within the shadow of time and progress. As overlooked gems become classics, and classics become worlds upon themselves, we recognize that Dylan at his worst is still better than most.

–Kristofer Lenz
Staff Writer


38. Dylan (1973)

Bob Dylan - Dylan

Dylan is a divisive singer and (at best) a mediocre guitarist. So why would he do an album full of covers? Blame the record company. After Dylan ditched Columbia for Asylum in ’73, his erstwhile label pieced together the LP from scraps and outtakes to sully Bob’s name and make a few bucks. Columbia was successful on both fronts: Dylan somehow sold more than 500,000 copies, yet it’s his most universally panned album. –Henry Hauser


37. Knocked Out Loaded (1986)

bob dylan knocked out loaded

Even Dylan’s less successful albums have some sort of audacious vision or greater artistic purpose that seeks to elevate or justify the work. It’s when this vision or purpose fails that an album is received poorly, but at least this intent stands and is worthy of recognition and discussion. The very worst of Dylan’s albums are those simply lacking in purpose. Case in point: Knocked Out Loaded. A collection of covers and songs that didn’t make the cut on other albums, Knocked Out Loaded is disjointed and grating (as Dylan pretends his voice isn’t going to shit). The only redeeming point is the epic “Brownsville Girl”. Co-written by Sam Shepard, it runs over 10 minutes and features Dylan at his narrating best as he unwinds an allegorical tale involving love, Gregory Peck, and a swirl of images and references. The song’s pace is patient as it perpetually builds toward a powerful chorus built upon a transcendent gospel choir arrangement. If only the rest of the album showed such purpose and vision. –Kristofer Lenz


36. Saved (1980)


Non-believers probably find Saved hard to stomach, but the 1980 release trumps any psalm posted on the hymn board at this week’s Sunday service. Dylan doesn’t ply the album – the second in his “Christian trilogy” – with religious allegory. Instead, he calls the shots like a celestial umpire. Jesus is the beginning and the end, and he wants everyone to raise their voices in exaltation right along with him (and his bevy of gospel babes). Recorded at Muscle Shoals Sound Studio with Jerry Wexler and Barry Beckett at the helm, Saved owes a heaping debt to Jesus Christ Superstar’s bombast, especially “Solid Rock”, which spreads the good news through a Johnny Otis hand-jive beat drunk on altar wine. –-Janine Schaults


35. Christmas in the Heart (2009)

bob dylan christmas in the heart 20 Ranking: Every Bob Dylan Album From Worst to Best

All the eggnog at Santa’s workshop couldn’t impair me enough to willingly listen to Christmas in the Heart again, despite Dylan donating all his royalties to several charities. I’d rather just cut them a check directly. Here, Dylan faithfully croaks through 15 traditional and secular Christmas classics, complete with sleigh bells and sugarcoated backing vocals. The only redeeming song to be found in Santa Bob’s magic bag is deranged polka “It Must Be Santa” with its rapid-fire call-and-response and delightfully madcap video. It’s an undeniably lousy novelty album but a terrific present for that jerk brother-in-law. –Matt Melis


34. Down in the Groove (1988)

bob dylan down in the groove

As this list attests, not all Dylan albums are created equal. Most consider Down in the Groove a throwaway, yet the 1988 release yielded two major developments. Mainly, its supporting jaunt kicked off the venerable Never Ending Tour, which Dylan treats like Forrest Gump’s running jag. No doubt, someday he’ll tire of the rigorous schedule and head home on a whim. The other silver lining is tucked away toward the end of the recording. “Silvio” paired Dylan with Grateful Dead lyricist Robert Hunter, who would return more than a decade later to collaborate on Together Through Life. The song, while in good hands here with Jerry Garcia and Bob Weir, really sprung to life in the late ’90s when stoic multi-instrumentalist Larry Campbell and hotshot guitarist Charlie Sexton flanked Dylan onstage. Sharply dressed in matching suits, their harmonies alongside Dylan’s growl created a sorely missed alchemy. –Janine Schaults


33. Under the Red Sky (1990)

bob dylan - under the red sky

Dylan admits that Under the Red Sky suffers from two major maladies: rushed recording sessions and too many cooks in the kitchen. The former was a product of his participation in supergroup The Traveling Wilburys, while the latter was producer Don Was’ misguided attempt to garnish the lackluster LP with star-studded cameos. But rather than salvaging the album, Elton John, George Harrison, David Crosby, Stevie Ray Vaughan, and Slash make it sound even more slipshod. –Henry Hauser


32. Empire Burlesque (1985)

bob dylan - empire burlesque

Seeking to glaze his ’85 LP with a modern sheen, Dylan initially recruited vogue DJ/producer Arthur Baker (New Order). Unfortunately, the result was Empire Burlesque, a contrived and awkward offering that stands out as one of the lower points in Dylan’s career. Buried beneath glitzy synths and obtrusive drums, the singer-songwriter’s lyrics are barely audible. The album feels forced, the instrumentation is puffy and bloated, and Dylan sounds like he’s just phoning it in. –Henry Hauser


31. Shot of Love (1981)

bob dylan shot of love

Dylan justified his Christian trilogy with the final song on its final album, “Every Grain of Sand”, possibly his prettiest composition ever, a Blakean shimmer of a song with spare instrumentation. Elsewhere on Shot of Love, which features guests like Ringo Starr and Ron Wood, the theology is a tougher sell, especially when Dylan is condemning non-believers on “Property of Jesus” (“You’ve got a heart of stone”). It’s not all about religion, as Dylan finds inspiration in a doomed counterculture icon on the piano ballad “Lenny Bruce”, for one, but the lasting impression is still one of piety. –Michael Madden


30. World Gone Wrong (1993)

bob dylan - world gone wrong

After emerging from an uneven ‘80s – as generous an assessment as you’ll find – and starting a fresh decade with the disastrous Under the Red Sky, maybe Dylan actually sought to avoid the spotlight and make himself as irrelevant as possible (wouldn’t be the first time). That would explain why he opted to turn out two albums of stripped-down, traditional folk covers (Good as I Been to You and World Gone Wrong) while the Seattle sound exploded all around him. While there’s little reason to revisit World Gone Wrong for its own sake, critics and fans alike have noted the darker themes and tones found in this collection, suggesting performances like “Blood in My Eyes” were precursors to Dylan’s resurgent late ‘90s output. A year later, Dylan would grudgingly make his triumphant MTV Unplugged return to public consciousness, and three years later he would be recording Time Out of Mind, his best studio record since Blood on the Tracks. Maybe something went right here after all. –Matt Melis


29. Together Through Life (2009)

bob dylan - together through life

Had Together Through Life been written and released a few decades earlier, this collaboration between Dylan and Robert Hunter might have been a game changer. These iconic lyricists stand tall among the best in American music history, and they’ve been friends for decades. Hunter is one of only two writers Dylan has collaborated with to this extent, the other being Jacques Levy on Desire in 1976. Perhaps with familiarity comes a touch too much comfort, as Together Through Life is carefully composed and performed, but has an almost blandly casual tone. The songs are tight and the lyrics right, but no single track would make a best-of list for either artist. Some highlights include the swaggering, swampy blues of album opener “Beyond Here Lies Nothin” and the moody sway of “Forgetful Heart”. Instead of a genre-redefining masterwork of two great lyricists, we have instead a sometimes engaging tour of American song styles and classic storytelling themes. –Kristofer Lenz


28. Infidels (1983)

bob dylan - infidels

On paper, Infidels should have been a triumphant return to form. It heralds the end of Dylan’s much-reviled evangelical Christian phase and incorporates elements of his newfound Judaical interests and even some of the social and political anger of his halcyon days of “finger-pointing” songs. His expert studio band was led by Mark Knopfler and included Mick Taylor on guitar and a rhythm section featuring reggae rockers Sly and Robbie. Despite the secondary support, the ’80s rock sheen of Infidels (crisp high hats and persistent synth melodies) have not aged well. The ranting songs skewer easy targets (Reagan on “Man of Peace” and the Middle East on “Neighborhood Bully”) and lack the biting cut of his previous work. While exquisite guitar work helps elevate the kabbalistic rumination of “I and I”, not a classic Dylan track is to be found. Infidels stands as an important turning point, setting the stage for the great, late albums to come, but on its own is mostly interesting for the exceptional production and performances from the band, and as a historic footnote. –Kristofer Lenz


27. Pat Garrett & Billy the Kid (1973)


After enlisting Quincy Jones to score his previous film, director Sam Peckinpah signed Dylan on to score his Western Pat Garrett & Billy the Kid and play Alias, a perpetually smirking cowboy. It hardly feels like a Dylan album; “Knockin’ on Heaven’s Door” is the only significant song here, while the rest passes like a woosh of vibrant acoustic guitar strums and strings, with singing here and there. Ironically, the vocal work that is here is some of Dylan’s most approachable, with (relatively) warm and steady tones. The math, however, is simple: While it won’t instantly prompt you to say adios, a Dylan record that lacks in lyrics is going to be lacking in general. –Michael Madden


26. Self Portrait (1970)

bob dylan - self portrait

Self Portrait creates more questions than it answers. Recorded soon after the country-inspired Nashville Skyline, Self Portrait represents one of the most confounding left turns in a career chock-full of them. This double album is comprised of oddly assembled covers and uninspired live performances. Dylan’s affected country croon does little to elevate any of the material. After one of the most remarkable, iconic, and consistent runs of releases, this 1970 release drops a jarring capstone on the glory of the 1960s. Largely reviled upon its release (“What is this shit?” wrote Greil Marcus in Rolling Stone), Self Portrait has earned some revisionist credibility as Dylanologists plumb the depths of the purpose behind this record. Was Dylan being ironic, lazy, or giving his fans and rock stardom as a whole a big middle finger? Purpose notwithstanding, Self Portrait offers little enduring value. –Kristofer Lenz


25. Fallen Angels (2016)

bob dylan fallen angels album new Ranking: Every Bob Dylan Album From Worst to Best

Shadows in the Night succeeded because it never settles for being just a curated sampler — a gimmicky album that could’ve been dubbed something like Bob Gets Frank. Instead, Dylan crafted a record with themes of pining, loneliness, and love kindled, lost, or enduring that cast long shadows deep into the night. He smoothed out his voice, stripped the arrangements of any excess, and tapped into what makes those sad songs eternal — as relatable to the rejected teen texting in his bedroom as the old man who only has worn photographs to remind him of a love that’s faded. A year later, those shadows have lifted, and Fallen Angels finds Dylan emerging from the gloomy stillness of winter into the relatively lighter air of springtime. Dylan may naturally be better at the brooding that Shadows required, but it’s still encouraging to see his once-broken protagonists emerge from their heartbreak and put themselves out into the world again. Ring-a-ding-ding, indeed. –Matt Melis


24. Good As I Been to You (1992)

bob dylan - good as i been to you

Leaving behind the pop rock sheen of the 1980s albums (and Under the Red Sky), Good as I Been to You was something of a breath of throwback air. His first acoustic album in nearly 30 years, this collection of covers is intimate in tone and precise in performance. The song selection is a story of its own, ranging from the mournful blues balladry of “You’re Gonna Quit Me” to the swinging bluegrass pace of “Step It Up”. Throughout, Dylan’s voice is natural as he transitions into accepting his raspy smoker’s-tone future, and his acoustic guitar work is entertaining, one of the better examples of his oft-mocked skills. With Dylan’s next-level songwriting chops, no collection of covers will ever be on equal footing as his best original work. Yet, recorded in his home studio, Good as I Been to You’s best quality is a conferred ambiance of sitting in the aged troubadour’s living room for a private performance of his favorite songs, the memory of which has endured all these years. –Kristofer Lenz


23. Street Legal (1978)

bob dylan - street legal

A year before entering his much-dissected Christian phase, Dylan delivered an album straight out of Sin City. Street Legal boasts all the trappings of a glitzy Las Vegas revue – sweaty sax, sultry backup singers with vocals dripping in gold lame – without the polished veneer of Elvis, who he’s so obviously trying to emulate. Critics like Greil Marcus had a field day trampling on the ’78 release’s woeful mix coupled with Dylan’s ragged delivery and periodically lazy rhymes. In Rolling Stone, Marcus pits it against Steve Martin’s “King Tut”, and the boy king comes out on top. However, the apocalyptic fever dream “Changing of the Guards” and gypsy march of “Senor (Tales of Yankee Power)” – a welcome staple of this century’s Never Ending Tour setlist – reveals Dylan’s sassy side. And that’s worth a dozen clunkers like “Is Your Love in Vain?” –Janine Schaults


22. Tempest (2012)

bob dylan - tempest

Tempest is no geriatric vanity project concocted to sell tickets to a grand world tour or stage a comeback. At 71, Dylan’s grizzled, bile-infused tone only accentuates his pointed observations and cinematic reeling. Number 35 on the roll call of his studio albums and released in 2012, Tempest finds the bard consumed by violence. The verses of the title track rearrange decades of scholarly research on the sinking of the Titanic, just like the ship’s pesky deck chairs, while “Tin Angel” painstakingly delivers a play-by-play of a triple murder-suicide. “Roll on John” pays tribute to the late Beatle – one of the only other humans alive or dead able to understand a grain of Dylan’s experience. Standing alone, sharp as ever, the songwriter closes this one out with a comma, not a period. –Janine Schaults


 21. Shadows in the Night (2015)

Bob Dylan Shadows in the Night

Nobody asked Bob Dylan to record an album of old standards popularized by Frank Sinatra. Not even the 50,000 randomly chosen AARP The Magazine subscribers who found a free copy of Shadows in the Night in their mailboxes. Then again, nobody asked Dylan to “go electric,” hole up with The Band in the basement of a pink house, or embark on a Never Ending Tour, either. Dylan has spent his entire career out of step with the rest of us — either prophetically ahead or anachronistically behind — to which we owe a sizable tract of our musical and cultural landscape. So, it’s with a certain faith that we followed Dylan once more, believing that going back in time through these old songs might lead us someplace new. After all, as he once sang, “The future for me is already a thing of the past.”

Dylan’s wisdom shows in his song selection. He opted to craft an album rather than curate a sampler. Consequently, themes of pining, loneliness, and love kindled, lost, or enduring cast long shadows throughout the record. His voice should by all rights be a liability on songs once sung by Sinatra. Rest assured, he has nothing on Ol’ Blue Eyes. But his vocals, less ragged than usual, fit the mood of this record better than expected, lending an everyman quality to these sentiments. While Shadows in the Night may ultimately be remembered as a brief detour on Dylan’s larger journey, it’d be a shame to dismiss this collection as a mere novelty or flight of whimsy. If nothing else, Dylan reminds us that men have been wrestling in the shadows with the complexities of the human heart long before we got here. –Matt Melis

20. New Morning (1970)

bob dylan - new morning

Long before The Big Lebowski used “The Man in Me” to transform bowling into ballet, New Morning ushered in a return to form a mere four months after the release of the critically vilified Self Portrait. The album’s 12 tracks sound like Dylan taking in a big breath of domestic tranquility and exhaling the burden of his elected omnipotent status. The genteel “If Not for You” stands as one of Dylan’s most concise, direct declarations of love, proving that while flowery verbiage and snarling cutdowns will win you the voice-of-a-generation crown, speaking straight from the heart will win you the girl every time. –Janine Schaults


19. Triplicate (2017)

bob dylan triplicate cover Ranking: Every Bob Dylan Album From Worst to Best

One can be a whim, and two an indulgence. But make no mistake about it: Three raises the ante to a phase, a period, an era. It’s difficult to believe that what began as a curiosity three years ago — a single Sinatra covers project — has now yielded three albums and 52 reimagined recordings of American easy-listening classics made famous by olive-oil crooners – all brought to you courtesy of the gravel-throated poet laureate of rock and roll. Here, Dylan not only triples down with his third consecutive and finest collection of traditional recordings but also with three distinct movements within the album, each a beautifully curated 10-song thematic set destined to be resolved by the following section. Dylan’s taste is impeccable, his voice strong, and his arrangements so enjoyable that it would be a shame if he never ventured down this particular road again. –Matt Melis


18. Oh Mercy (1989)

bob dylan - oh mercy

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 (John Cusack) sitting in a downpour during “Most of the Time”; gentle lament “Shooting Star” and the Hawthorne-indebted “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 a bit. Oh, mercy, mercy me. –Matt Melis


17. Slow Train Coming (1979)

bob dylan - slow train coming

If Bob Dylan’s born-again phase had begun and ended with Slow Train Coming (thereby delivering us from Saved), we might look back upon those days more fondly. However, hidden beneath the overt proselytizing and the less-than-subtle cross-shaped pickax swung by the railroad worker on the cover art is a better album than anything Dylan would release during the upcoming decade. While songs like “Gotta Serve Somebody”, “Slow Train”, “Precious Angel”, and “I Believe in You” all carry obvious religious themes, it’s also possible to listen to them as sociopolitical or romantic declarations, and nobody can deny that Slow Train features some of Dylan’s most impassioned singing ever. Clearly Bob had caught the spirit. We just wish he hadn’t held onto it for quite so long. –Matt Melis


16. Planet Waves (1974)

bob dylan - planet waves

Backed by Rick, Robbie, Richard, Levon, and Garth, Bob Dylan’s ’74 offering, Planet Waves, shot up to No. 1 and brimmed with sloppy heaps of accordion, harmonica, and scratchy guitars. The album kicks off with “On a Night Like This”, as Dylan and The Band unleash some Basement-era weirdness. The down-tempo “Dirge” is an often-overlooked lyrical highlight, but the LP’s linchpin is “Forever Young”, which concludes Side 1 (slow version) and commences Side 2 (fast version). As Dylan nears middle age, the song conveys his struggle to stay true to himself in a world that just keeps on a-changin’: “May you have a strong foundation/ When the winds of changes shift.” –Henry Hauser


15. Modern Times (2006)

bob dylan - modern times

With Modern Times, his third consecutive late-career triumph, Dylan settled into his seniority and recorded 10 songs that are virtually all substance, no style; even “Love and Theft” had flashy moments by comparison. Sure, there’s an elegance in the arrangements and the band’s interplay (see the jaunty “Spirit on the Water”), but the chord progressions and steady drums form rollout mats for his verses of romantic/social disillusion, carriages of instrumentation that hardly seem to dictate his mood or intensity level. If the old man feels empty, it helps that these songs have glimmers of his sense of humor: “I can’t go to paradise no more/ I killed a man back there,” he shrugs on “Spirit in the Water”. True enough, the peak of his songwriting and relevance was decades behind him, but he was carrying on with purpose, writing songs that seemed to be therapeutic for him. –Michael Madden


14. Bob Dylan (1962)

bob dylan - bob dylan

With just two all-original songs, the straightforward biography of “Talkin’ New York” and the reverence of “Song to Woody” (most likely the first song he wrote after making his way to New York in January 1961), the rest of Dylan’s debut found the 20-year-old eager to make a name for himself in Greenwich Village’s folk revival, covering blues singers of decades past (Blind Willie Johnson, Blind Lemon Jefferson) as well as the folk scene’s favorite traditionals. He would release The Freewheelin’ Bob Dylan the next year and display a stunning leap in songwriting ability and political acuity, but even the bleakness he brings to “House of the Risin’ Sun” shows he knew how to handle a heavy topic when he heard one. –Michael Madden


13. “Love and Theft” (2001)

bob dylan - love and theft

“Sky full of fire/ Pain pourin’ down,” sings Dylan on “Love and Theft” standout “Mississippi”. The line almost seemed prophetic when the record came out on September 11, 2001. Coincidences aside, though, “Love and Theft” cemented Dylan’s late-era resurgence, assuring listeners that 1997’s Time Out of Mind hadn’t been a fluke. Even grittier and dirtier than its blues rock predecessor, the record roars through an old-time South whose gentility has been corrupted and sullied by an album’s worth of rogues, scoundrels, and treacherous women who bring only pain. It’s dark, humorous, romantic, and up to its neck in biting contempt. –Matt Melis


12. John Wesley Harding (1967)

bob dylan - john wesley harding

John Wesley Harding wasn’t just Dylan’s first album after his mysterious motorcycle crash of ’66. It was also the first album with which he seemed to take a deliberate step backward. It’s the product of an in-and-out studio process – recorded on three separate days in fall 1967 at Nashville’s Studio A – and features straightforward, country-indebted songs accompanied by a small circle of musicians (including “Desolation Row” guitarist Charlie McCoy). The most enduring song is without a doubt “All Along the Watchtower” – a quick-striking example of Dylan’s narrative ability, an unsettling vision of a joker and a thief – but there’s a distinct charm to the breezier numbers too, including the Ray Charles-style blues “Down Along the Cove”. –Michael Madden


11. Another Side of Bob Dylan (1964)

bob dylan - another side of bob dylan

Another Side of Bob Dylan is anchored by a slew of individualistic “post-protest” songs that marked a major departure from the topical “finger-pointing” tunes of his first three albums. Rather than chronicling the societal ills of bigotry, injustice, and militarism, Dylan explores internal psychological conundrums and quagmires. “My Back Pages” is a raw, brutal critique of the protest movement itself. The song opens with a scratchy acoustic guitar hook that contrasts the crisper sound of The Times They Are a-Changin’, as the folk troubadour satirizes his fiery protest-era self in the opening verse: “Crimson flames tied through my ears.” He howls in painful recognition that aggression, even against malignity, only spurs animosity and intolerance. With great sorrow, Dylan admits to having held the belief that the moral and the iniquitous could be categorized and separated: “Good and bad, I defined these terms/ Quite clear, no doubt, somehow.” The real world, Dylan recognizes, is not that simple. Allies are exposed as enemies, promises transform into empty words, and morals shift and sway with the blowing of the wind. –Henry Hauser


10. Nashville Skyline (1969)

bob dylan - nashville skyline

Around Dylan, America burned. 1968 and 1969 were two of the most tumultuous years of social and political upheaval in America’s history. Once a political firebrand, Dylan chose not to wrap himself in the flag of the resistance and stand alongside his former brothers-in-arms. Instead of throwing fuel on the fire, he offered something more akin to a salve. After a decade of writing some of the most dense and moving songs in rock history, Nashville Skyline appears as a breath of fresh air. A moment’s respite where poet, prophet, and politico Dylan visits a simpler but no less beautiful style. These country-inspired songs offer little artifice or misdirection and instead offer open, big-hearted sentiment. The saccharine but effective “Lay, Lady, Lay” would become one of Dylan’s biggest commercial successes, but the real gem is album closer “Tonight I’ll Be Staying Here with You”. Here we get Dylan with a wry, unironic grin telling a story about a one-night stand that promises to be more. Clocking in at a mere 27 minutes, Nashville Skyline is full of simple, sweet pleasures. –Kristofer Lenz


09. The Basement Tapes (1975)

bob dylan - the basement tapes

In 1967, with just about every band around them seeking ways to add color and volume to rock (see Sgt. Pepper’s and Are You Experienced?), Dylan and The Band returned to the genre’s roots, free of any record company’s desires and able to do what they damn well pleased. That usually meant paring down both music and lyrics to the essentials: melody and progression rather than texture and force. You can hear pure joy in Robbie Robertson’s guitar solos and individual licks, for example, because there’s no reason to believe he’s doing it for anyone besides himself and his bandmates: no money was promised, no onlookers to impress. It was pure, music for music’s sake – it sounds corny, but really, these were ideal conditions.

That meant the spring and summer sessions were filled with giddiness and gaffes – even The Basement Tapes, the official double album released at long last in 1975, is filled with cracking voices and relaxed guitar progressions to go along with the smoother performances. Accordingly, the lyrics often seem meaningless, even downright silly, but there are still these names (including blues empress Bessie Smith and one “Katie”) and places (particularly the far-off paradise of Acapulco) that give it a lonesome heartland quality.

We can debate whether or not any of the songs on the official album should have been replaced by other songs from the sessions (“I Shall Be Released” and “I’m Not There” are among the most popular omissions). Regardless, The Basement Tapes proper is a collection that, at over 70 minutes, asks you to delve into a history that’s still unfolding – see this week’s release of The Basement Tapes Complete: The Bootleg Series Vol. 11, a six-disc document of practice making perfect. –Michael Madden


08. Time Out of Mind (1997)

bob dylan time out of mind 1997 Ranking: Every Bob Dylan Album From Worst to Best

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


07. Desire (1976)


Desire‘s opening and closing tracks represent the duality of Bob Dylan’s songwriting legacy like bookends. The serpentine “Hurricane” uncovers Dylan the activist after many years of shying away from topical material. In 1976, he again crusades for one man’s freedom in the face of racial injustice by wielding words as irrevocable as those pistol shots ringing out in the night of the murders that would eventually land Rubin “Hurricane” Carter in the slammer. Dylan’s dedication to liberating the former middleweight boxing contender from incarceration is synonymous with the album and the coinciding hippie caravan dubbed the Rolling Thunder Revue. Despite the tour’s two star-studded benefit concerts in his honor and the nearly nine-minute caterwauling epic, Carter didn’t gain freedom until 1985.

Dylan’s wistful love songs always hinted at his penchant for romance, but nothing matches the raw emotional plea of “Sara”. The dirge, buoyed by album linchpin Scarlet Rivera’s haunting violin, ends Desire on a desperate note. Dylan provides a revealing, if not nostalgic, look at his marriage to Sara Lownds and practically grovels to keep it intact. It’s a switcheroo from the venom spewed a year prior on Blood on the Tracks. Here he also makes the startling admission that the titular woman inspired “Sad-Eyed Lady of the Lowlands”.

He’s less forthcoming on the album’s remaining selections, preferring to hide amongst mythical (“Isis”) and real-life (“Joey”) characters in exotic locales (“Mozambique” and “Romance in Durango”). Most surprisingly, Dylan’s attitude toward women softens on this collection. Chalk it up to the presence of Rivera and the silken-voiced Emmylou Harris or co-writer Jacques Levy, but he’s mellowed out on the feminine mystique. On “Oh Sister”, as Dylan and Harris’ vocals circle each other like cautious felines, he’s extending a platonic olive branch for once instead of licking some wound or crying sour grapes. –Janine Schaults


06. The Freewheelin’ Bob Dylan (1963)

bob dylan freewheelin Ranking: Every Bob Dylan Album From Worst to Best

Bob Dylan pulls no punches on his scathing ‘63 album, The Freewheelin’ Bob Dylan. Quack psychoanalysts (“Talkin’ World War III Blues”), war hawks (“Masters of War”), and segregationists (“Oxford Town”) are all exposed to Dylan’s wrath.

Freewheelin’ also showcases Dylan’s rakish sense of humor. Take the waggish, droll closing number “I Shall Be Free”, an instrumentally sparse ditty featuring Dylan’s anemic, jumbled vocal delivery and a torpid, downtrodden harmonica. Joking around about the stagnant US economy, Dylan describes JFK’s seemingly straightforward question: “My friend, Bob, what do we need to make the country grow?” Always the lewd prankster, Dylan’s deadpan reply is a trio of ’60s sex symbols, one French, one Swedish, and one Italian: “Brigitte Bardot, Anita Ekberg, Sophia Loren/ Country’ll grow.”

“Don’t Think Twice, It’s Alright” features the cool, languid fingerpicking of session man Bruce Langhorne set against a slow, deliberate melody that envelops the track in a disarming nostalgia. While filled with sadness and longing, Dylan tempers these feelings of dejection by assuring us that getting dumped isn’t the end of the world. Wounds heal, we move on, and the molten rage cools. In the end, it’s usually alright.

Many of album’s most lasting and prophetic cuts concern the subject of war. Decrying American militarism, the quartet of “Masters of War”, “Blowin’ in the Wind”, “Talkin’ World War III Blues”, and “A Hard Rain’s a-Gonna Fall” offers chilling insight into war, its roots, and its victims. Set to a stark, malevolent acoustic guitar, “Masters of War” takes dead aim at America’s military-industrial complex and the barons it enriches. Relying on a series of abstract rhetorical questions to denounce meaningless brutality and aggression, Dylan sounds frustrated and wounded on “Blowin’ in the Wind”. Pillaging slave spiritual “No More Auction Block” for a melody, Dylan yearns for a future where guns and bombs, not books and songs, are banished: “Yes, how many times must the cannon balls fly/ Before they’re forever banned?”

Recounting a surreal dream from the vantage point of his psychiatrist’s couch, “Talkin’ World War III Blues” has Dylan singing of a fictitious landscape ravaged by war. Repelled at gunpoint when approaching a fallout shelter and shunned as a Communist, Dylan envisions a harsh and paranoid dystopia. And then there’s “A Hard Rain’s a-Gonna Fall”, apocalyptically described by Dylan as being about “some sort of end that’s just gotta happen.” Sharply contrasting a lithe melody with lyrics of “guns and sharp swords in the hands of young children” and “pellets of poison” floating in the sea, Dylan frighteningly rifles through the horrors of war. –Henry Hauser


05. The Times They Are A-Changin’ (1964)


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.” His entire 1964 album of the same name – 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


04. Blood on the Tracks (1975)

blood on the tracks album cover1 Ranking: Every Bob Dylan Album From Worst to Best

The divorce record by which all other releases documenting the disintegration of a relationship are measured, Blood on the Tracks bears the burden of being singled out as one of Bob Dylan’s crowning achievements and, in list upon best-of list, one of the all-time greats. The double entendre of the title says it all: Dylan smeared his blood, sweat, and tears all over the album’s 10 tracks. Reeling from the sour turn his nine-year marriage to former model Sara Lowndes took, Dylan lives out the five stages of grief in song, veering wildly from riotous indignation (“Idiot Wind”) to measured acceptance (“If You See Her, Say Hello”). Reaching the top spot on the Billboard 200 charts upon its debut in 1975, fans clamored for this unvarnished peak into Dylan’s broken heart. Later, he admitted, “A lot of people tell me they enjoy that album. It’s hard for me to relate to that, you know? I mean, people enjoying that type of pain?”

The recording sessions matched the anguished mood of Dylan’s compositions. Returning to the scene that birthed many of his ’60s classics – New York’s A&R Recording Studios – with the legendary John Hammond in the wings and members of Deliverance, Dylan raced through the sessions, changing direction mid-verse and kicking the musicians to the curb when they failed to keep up. On the advice of his brother during a Minnesota visit, Dylan enlisted some locals to re-record a few tunes with substantial lyrical changes. The final product is a hodgepodge of East Coast and Midwestern styles.

Dylan often denies the album’s autobiographical elements as if his private life wasn’t fodder for gossip long before TMZ rolled into town. Not that one needs to envision the couple’s real or imagined strife to marvel at the beauty he twists out of trauma. Like the angel beckoning Dylan to come in from the wilderness, Blood on the Tracks serves as a shelter from the storm of biting loneliness. –Janine Schaults


03. Bringing It All Back Home (1965)

bob dylan - bringing it all back home

Bringing It All Back Home has Bob Dylan yearning to break free from a society in shambles. Seeking refuge from the repulsive inauthenticity blanketing every aspect of American life, Dylan retreats within the bounds of his own mind.

In “Mr. Tambourine Man”, Dylan describes a limitless landscape apart from society. Liberated from worries and cares, he shamelessly requests to hear a tune. Ties to the outside world are gladly chucked aside, as we surrender our full attention to Dylan’s tranquil fingerpicking. It’s a fresh start, an escape from those “ancient empty street’s too dead for dreaming.” This is a place where our physical bodies no longer come into play – we’re transcendent (“My senses have been stripped/ My hands can’t feel to grip”). Rather than seeking solace in the company of his peers, Dylan searches for inner peace within his psyche.

Featuring neo-Beat incantations (“Gates of Eden” and “It’s Alright Ma”), smitten love ditties (“Love Minus Zero / No Limit” and “She Belongs To Me”) and a whimsical stream of consciousness epic (“Bob Dylan’s 115th Dream”), the LP is as diverse as it is deep. And those rambling admonitions on “Subterranean Homesick Blues” – Dylan’s first single to chart in the US – provide at least as much guidance as Poor Richards’ Almanac or the King James Bible.

A gentle, solemn tempo begins closing cut “It’s All Over Now, Baby Blue”, as Dylan lulls us into a trancelike state. In a raspy monotone, the singer appears to be delivering a requiem. He urges immediate escape: “You must leave now, take what you need you think will last.” The full spectrum of Dylan’s emotions floods a bluesy harmonica, peppering the track with a sense of unrecoverable loss. Everything you have come to rely on now lays in ruins. But although Dylan sings in a mourning timbre, the song ends on a hopeful note of individual rebirth and a chance for redemption: “Strike another match, go start anew.” Just four months later, Dylan took his own advice in starting anew in a major way: he went electric at the ‘65 Newport Folk Festival. –Henry Hauser


02. Highway 61 Revisited (1965)

bob dylan - highway 61 revisited

Whereas half of Bringing It All Back Home was electric, eight of this album’s nine songs are, to some extent, plugged in. The other, “Desolation Row”, seems to have a locomotive force of its own. Whether or not Dylan was a sellout for ditching the folk revival in favor of the new direction, he was absolutely unrelenting, determined to innovate even more than he already had.

He succeeded, and you can thank the sheer force for that: There was loads of bludgeoning instrumentation, with the likes of doomed guitarist Mike Bloomfield and drummer Bobby Gregg exploding holes in the opening stretch of “Like a Rolling Stone”, “Tombstone Blues”, and “It Takes a Lot to Laugh, It Takes a Train to Cry”. As easy as it is to picture Dylan conceiving, developing, and finalizing his vision for these songs by himself, his band had a seismic impact whether or not the individual contributions were planned — see the organ playing of Al Kooper, who was never formally enlisted to contribute those melodious chords on “Like a Rolling Stone”.

Even with the surreal detail of “Mr. Tambourine Man” and “It’s Alright, Ma (I’m Only Bleeding)” in the rearview mirror, 61 also marked a shift in Dylan’s lyrical approach. There are the towering word counts of “Like a Rolling Stone” (originally a “piece of vomit” totaling some 20 pages) and the 11-minute, 10-verse “Desolation Row”, and every song is filled with culture references and imagery. If you like gossip, you can spend a long time trying to decode “Like a Rolling Stone” and “Queen Jane Approximately” to see if they really are about Edie Sedgwick and Joan Baez, respectively. You can also analyze “Ballad of a Thin Man” for Dylan’s interpretation of the media – or maybe it’s just a delirious swirl of crooks, lepers, F. Scott Fitzgerald, and any and all qualities they may share. With 61, conclusions tend to be unreachable, but at least one thing is for sure: In their trail of destruction, Dylan and co. left piles of clues for contemporaries who wanted to figure out how they masterminded it all. –Michael Madden


01. Blonde on Blonde (1966)

blonde on blonde Ranking: Every Bob Dylan Album From Worst to Best

Pick up the record in its sleeve and there is a heft, an unusual weight for a rock ‘n’ roll record. On the cover, we see Dylan — smugly pursed lips, casually wrapped scarf, and that big mop of black hair mussed just-so — and he meets our gaze. He stares back, if not haughtily, then expressionless. But we cannot meet his gaze. The photograph is just slightly blurry, leaving one to rub and squint eyes, but no clearer vision comes. Held here is the ultimate culmination of the shifting, infinite possibilities of Dylan’s trickster persona. In this blurry, mind-bending image, we perceive the clearest vision of the artist ever offered.

1965 and 1966 were the artistic peak for Bob Dylan. A flurry of production and self-examination produced three of the great rock ’n’ roll albums in history, culminating with Blonde on Blonde. In this record, we hear the rattling, dying gasp of Dylan the folk hero as rock god status consumes him fully, irrevocably. In it we hear Dylan the writer/politico/agitator become Dylan the poet, as his wild, hallucinatory lyrics begin a dance of allusion and discovery that pierces the plane of art, finding a level he would never rival again. In it we hear the past, present, and future of American music as the rearguard of Americana pushes up through the frontlines and emerges into the avant-garde. It is a work of such powerful vision that lists of grandiose platitudes (like this one) are carefully wrought in an effort to leave a vague, smoky swirl around the album’s grand shape — but no summary or description can hope to touch, nevertheless contain.

For the clarity and precision of its vision, Blonde on Blonde was assembled haphazardly. The story of its making is alive with its own mythology. Dylan cranking out lyrics in a hotel room or in the studio itself, possibly dreaming of the decline of his “relationship” with Edie Sedgwick (and is noticeably absent of devotion to new wife Sarah Lowndes). The impressive array of studio musicians, including Robbie Robertson and Al Kooper, mixed and matched instruments and lines with the rest of the Hawks and a long list of talented Nashville sessions musicians. Was the epic 11 minutes of “Sad-Eyed Lady of the Lowlands” truly recorded in one take?

The resulting looseness, in composition and performance, is the album’s greatest charm. The best art does not resolve itself. Instead it stays alive and open to interpretation, discussion, argument, and re-interpretation. On Blonde on Blonde, the sound wriggles beneath one’s grasp. The closer one listens the more difficult it is to isolate the parts comprising the exultant yet funereal New Orleans march of “Rainy Day Women #12 and #35”. The snaking and interlaced organ and guitar riffs of “Stuck Inside Mobile with the Memphis Blues Again” create a sonic ouroboros, bringing us always back again. The album swings wildly around musical themes, including swampy blues (“Pledging My Time”), a mournful torch song (“One of Us Must Know (Sooner or Later)”, and screeching garage rock (“Obviously Five Believers”).

And above it all, lyrically Dylan has never been finer. In the mounting verses of Blonde on Blonde, Dylan is alternately funny, irreverent, serious, heartbreaking, sexist (?), and, finally, profound. No single song lacks the potential for or does not reward deep examination. Even the seemingly slight “Rainy Day Women #12 and #35” offers endless interpretation (funny? ironic? earnest?). Throughout, the cast of narrative characters he had created to this point, whom we would hear from again and again, bound effortlessly through each verse. The jester, Shakespeare, the River Boat Captain, Johanna, and so many others stop by, check in, and fade into darkness again.

It is the last of that list, Johanna, who leaves the deepest impact. In the swirling epic “Visions of Johanna”, Dylan is at his most poetic and inscrutable. Of course, Johanna herself is nowhere to be found. Instead she serves as a representation, an untouchable essence as we chase “Louise” and her paramour. Attempting to follow the narrative is one path, but another is letting the waves of surreal images wash over you and making them your own. Lines like “The ghost of electricity howls through the bones of her face” and “Inside the museum infinity goes up on trial/ The voices echo, ‘This is what salvation must be like after a while’” exist in a space far beyond their reckoning. Wrested free of their embedding in Dylan’s art, they take new life with each listener. At his best, Dylan tells us the stories of our own lives. On Blonde on Blonde, he creates an alternate life and persona for himself and his listeners, explaining our lives, our motivations, our selves, in ways we would have never imagined otherwise. –Kristofer Lenz

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