A guide to the complete albums of Bob Dylan
The influence of an artist like Bob Dylan is nearly immeasurable. In his six-decade career, he’s released nearly 40 albums, collaborated with just about everyone, from Mark Knopfler and members of The Beatles to reggae rhythm section Sly and Robbie and punk band The Plugz, and he’s changed his sound every few years or so. He launched his career in the Greenwich Village folk scene of New York City in the early 1960s, went electric and made at least one dude mad in the process, went country, recorded a bunch of covers, became a born-again Christian and then took any number of other turns toward brilliance ever since. There’s also a Christmas album in there somewhere. If it’s an exaggeration to say that Dylan has done it all, it’s only a slight one.
But even more than that, he’s one of the greatest songwriters that America’s ever produced. Shortly after he began playing covers of folk standards, he quickly built up a catalog of his own classics, which range from socio-political commentary (“Masters of War”) to a more personal form of storytelling (“Tangled Up in Blue”) to the kinds of fascinatingly cryptic tomes that fans would discuss for decades to come (“Ballad of a Thin Man”). Even when you account for a song like “Wiggle Wiggle,” which I grant you is a head scratcher, the number of absolute masterpieces remains staggering.
As this year is the 60th anniversary of two of his greatest albums, Highway 61 Revisited and Bringing It All Back Home, we took the opportunity to dive into Dylan’s complete catalog, from his early folk days on up to his late-career resurgence and forays into standards and even Christmas music. It’s a group effort, and we had many internal discussions and debates in order to come up with a complete picture: the hits, the misses, the underrated and the wild pitches.
We kept our hot takes to a minimum, but it wouldn’t be a Dylan feature without at least a couple. And we don’t necessarily expect everyone to agree; some albums we have more affection for than we realized. Some, however, haven’t held up as well. With a giant like Dylan, there are bound to be some differences of opinion, and we opted not to fight it. So we hope you enjoy either way—get comfortable and settle in for a deep dive through our complete Bob Dylan album guide.
Note: When you buy something through our affiliate links, Treble receives a commission. All albums we cover are chosen by our editors and contributors.
Bob Dylan (1962)
Recorded when he was only 20 years old, Bob Dylan’s self-titled debut is the one that best reflects his roots in the Greenwich Village folk scene in New York in the early 1960s, its tracklist a veritable history of folk ballads including the likes of “In My Time of Dying,” “Man of Constant Sorrow” and “House of the Rising Sun.” We only get the faintest flashes of Dylan’s songwriting talent, with two originals: “Talkin’ New York,” a talking-blues-style song he’d continue to develop over the next three years, and “Song to Woody,” a tribute to Woody Guthrie (and Cisco Houston, Sonny Terry and Lead Belly), that stands as the first glimpse of his greatness to come. But mostly, the album is a snapshot of Dylan as folk scholar, a one-man songbook that he’d translate into a singular body of work of his own soon enough. – Jeff Terich
Rating: 8.3
Listen/Buy: Spotify | Rough Trade (vinyl)
PIN ITThe Freewheelin’ Bob Dylan (1963)
The world bore witness to Robert Zimmerman’s transformation to Bob Dylan on his self-titled debut album in March 1962. Fourteen months later is when Dylan really became Dylan, delivering an embarrassment of songwriting riches on his second album. Close to half of The Freewheelin’ Bob Dylan could be included in a protest music greatest-hits, building on folk and blues traditions to show off an awakening political awareness. But scattered amid arm-linking anthems like “Blowin’ in the Wind” and “Masters of War,” Dylan also proved adept at addressing the niceties and not-so-niceties of love in “Girl from the North Country,” “Don’t Think Twice, It’s All Right,” and more. And while he introduces a backing band for the first time on “Corinna, Corinna” (a few years ahead of what would be his controversial “electric” shift), it’s not lost on me that he commands so much attention with just his voice, guitar, and a harmonica that’s part jaunty melody, part alarm, part train whistle of wanderlust. – Adam Blyweiss
Rating: 10.0
Listen/Buy: Spotify | Amazon (vinyl)
The Times They Are A-Changin’ (1964)
We debated this entry long and hard ‘round the Treble offices. Released in 1964, Times came arrived less than 12 months than the towering monument that is Freewheelin’ and its coterie of easy-singin’ classics. Hence, it’s tempting to think that these ten songs pale in comparison. However, upon deeper reflection, you see have deeper roots in vintage folk and country than its predecessor, complete with drone strings, open tunings, murder ballads, and campfire singalongs. Excellent tunes like “With God on Our Side,” “Boots of Spanish Leather,” and “The Lonesome Death of Hattie Carroll” overflow with sharp wordplay, plaintive vocals, and tender harmonica. And when it comes down to it, the title track is the most recognizable song in Dylan’s entire canon, with a chord progression and lyrical truths that will never grow old—no matter how much times change. – Adam P. Newton
Rating: 10
Listen/Buy: Spotify | Turntable Lab (vinyl)
Another Side of Bob Dylan (1964)
It is as it promises: another side, an attempt by a young Dylan to expand beyond his already-mastered social commentaries and harrowing blues. Some of that is retained here and it’s as masterful as ever; see “Chimes of Freedom”. But we also get his early flawed stand at roiling epics and humor and joviality, all of which would be sharpened to perfection soon enough but here are still mere prototypes. Plus following Times, arguably the greatest American folk record of all time, diminishes even bright lights. – Langdon Hickman
Rating: 9.2
Listen/Buy: Spotify | Amazon (vinyl)
Bringing It All Back Home (1965)
A year before the “Judas!” incident, Bob Dylan fleshed out his folk songwriting with proper full-band rock arrangements, kicking off his fifth album with the rollicking “Subterranean Homesick Blues,” which despite any perceived slight on the part of the folk community (at this point it seems beyond overblown), was actually Dylan’s first charting U.S. single. But Bringing It All Back Home is Dylan offering the best of his two sides (literally): acoustic troubadour and fired-up rock bandleader. His songwriting hit an early peak here that would continue throughout the 1960s, adapting rapid-fire streams of imagery and clever social critiques to rowdier rock arrangements or even sweeter, prettier moments like “Love Minus Zero/No Limit.” However much side A turned Dylan’s folkster image on its head, side B reaffirms him as one of the best to ever strum an acoustic guitar, all four of its songs among the best he ever wrote, particularly the hypnotically acerbic “It’s Alright Ma (I’m Only Bleeding)”, littered with inspired moments of lyrical cynicism like “Although the masters make the rules, for the wisemen and the fools.” Not Dylan’s first masterpiece, but arguably his most important. – Jeff Terich
Rating: 10
Listen/Buy: Spotify | Turntable Lab (vinyl)
Highway 61 Revisited (1965)
On Highway 61 Revisited, Dylan doubled down on the electrification experiment he began with Bringing It All Back Home, much to the chagrin of folk purists. While the album is often talked about as marking a watershed moment in the mid-1960s emergence of the counter-culture and the protest movement, the lyrics of songs like “Like a Rolling Stone” and “Queen Jane Approximately” were more personal than political in nature. Dylan had assembled a band of musicians together who all clearly knew what they were doing at this point, and his confidence in them was evident from his being empowered to branch out into the uptempo blues of “Tombstone Blues” and the boogie-woogie of the title track. Epic closer “Desolation Row” showed he hadn’t completely severed ties with his folk roots, however. While its then-iconoclastic nature might be difficult for modern-day listeners to appreciate, Highway 61 Revisited remains one of the finest demonstrations of Dylan and his collaborators’ songwriting abilities and musicianship. – Greg Hyde
Rating: 10
Listen/Buy: Spotify | Turntable Lab (vinyl)
Blonde on Blonde (1966)
Blonde on Blonde isn’t just one of the greatest records of all time but, along with bedmates like Pet Sounds and Sgt. Pepper, one of the releases that shaped how we even interpreted what an album was. It’s a technicolor wheelhouse, a menagerie of sorrows and libations, tin whistle and song, while the unnamed main figure is worn and wearied by a harrowing strange world. The final side, the single-song “Sad-Eyed Lady of the Lowlands,” one of the progenitors of progressive rock, holds the key: love, only love, can save us amidst the arrows of samsara, our souls strapped to that breaking wheel. I didn’t even mention the musicianship of the young Hawks, soon to be The Band. There’s simply too much perfect to ever note it all. – Langdon Hickman
Rating: 10
Listen/Buy: Spotify | Turntable Lab (vinyl)
John Wesley Harding (1967)
John Wesley Harding is cursed by chronology. It can’t possibly live up to its predecessor Blonde on Blonde. It was recorded concurrently with some of The Basement Tapes, to which it’ll also never be equated. Yet it contains songs now counted as some of Dylan’s best (or at least better) work: “All Along the Watchtower,” “As I Went Out One Morning,” the title track, and “I’ll Be Your Baby Tonight.” The arrangements, while spare and acoustic, are often rollicking, in no small part due to the brisk bass and drums, respectively, by Nashville A-Teamers Charlie McCoy and Kenny Buttrey. Ultimately, one of Dylan’s most subtly cohesive albums, with lyrics embodying the stranger corners of America (historical and current) even at their more surreal. – L.D. Flowers
Rating: 8.6
Listen/Buy: Spotify | Rough Trade (vinyl)
Nashville Skyline (1969)
The backstory is enough of a selling point: voice-of-a-generation-turned-traitor-turned-recluse comes out of the woodwork and releases what amounts to an EP of candy-coated country toss-offs sung in the voice of a fake crooner. But against all odds, Nashville Skyline is one of Dylan’s best albums, modest but entirely successful in its goals. Every song is pleasant to listen to, though two stand the test of time apart from the country conceit, both resurrected in equally amazing form during the Rolling Thunder tour several years later: “I Threw It All Away” and “Tonight I’ll Be Staying Here With You.” Undoubtedly, it’s less deep than anything that came before. But to call Nashville Skyline an about-face is to assume there was a planned path to begin with. Dylan has always known his work’s trajectory is his alone to chart. Just three years prior, going electric changed everything. But in some ways, Nashville Skyline is the new beginning that really counts: the birth of Dylan as playful genre experimenter, the Dylan we still have today. – Casey Burke
Rating: 9.2
Listen/Buy: Spotify | Amazon (vinyl)
Self Portrait (1970)
Ask 10 Dylan fans which album is his worst and you might get 10 different answers (unless live albums are in the mix and then they’d all say Dylan & the Dead). But at least one would say Self Portrait. For the better part of a decade or longer, that was simply accepted fact: Dylan followed a decade’s worth of great-to-perfect albums with a rambling mess of covers, cast-offs and other ill-conceived flights of fancy into a 2xLP length mish-mash of this and that. Part of the problem is the idea of this being a studio album rather than a compilation of outtakes and rarities; Dylan himself once referred to Self Portrait as akin to releasing his own bootleg, and the raw live recordings included bear that out. But boy is it a mess; why is “Little Sadie” on here twice? And is one of them so much worse than the other? Why does the live recording of “Like a Rolling Stone” sound like Dylan: The Vegas Revue? Why does his singing style keep ricocheting back and forth between his signature style and his Nashville Skyline croon? Still, there’s plenty to like: “Copper Kettle,” “Days of ’49,” and “Wigwam,” which probably helped rehabilitate the album’s image given its use in The Royal Tenenbaums. There’s a good album in Self Portrait, but he makes us dig for it. – Jeff Terich
Rating: 6.1
Listen: Spotify
New Morning (1970)
Despite winning back fans he might have lost with Self-Portrait, New Morning was a difficult and imperfect album to cobble together. Dylan would find himself in conflict throughout, against his studio hands, his business manager, and the producer of a play from which he removed his music and brought in part here. There are stretches of New Morning where short songs feel like undercooked demos, and other moments where his backup singers torpedo work with the feel of sonic self-parody. But we can also tell his folk trappings have morphed here into a more detached kind of storytelling and thematic exhortation. The lyrical cadences seem simpler than his politicized folk peak, even the religiously-inflected writing seems observational and straightforward, and Dylan and his band promote piano and organ over his signature harmonica and guitar picking. This album more than most feels like a temporally logical result of Dylan “going electric” a few years prior. Songs like “If Not for You,” “Three Angels,” and “Day of the Locusts” are important not because of how Dylan sussed out music for himself, but how he presented it as a template for a bright line of hardscrabble singer-songwriters—the likes of Billy Joel, Tom Waits, Randy Newman, and Bruce Springsteen, all of whom would debut over the next three years with sounds you heard here first. – Adam Blyweiss
Rating: 7.3
Listen/Buy: Spotify | Amazon (vinyl)
Pat Garrett and Billy the Kid (1973)
In the aftermath of his mid-’60s explosion, Dylan attained a new kind of career freedom. Born from the same recording sessions, 1970’s New Morning and Self Portrait showed a goofy lightness and a newfound willingness to play with genre. Following those albums up with Pat Garrett and Billy the Kid, the soundtrack to Sam Peckinpah’s cheesy 1973 western of the same name, made perfect (non)sense. But the end result is a missed opportunity—better than the movie but lacking the impish spark that animates the best moments in his early ‘70s work. It sounds like a grab bag of mostly Dylan-lite instrumentals, impressions of himself. Except, of course, for the still-ubiquitous “Knockin’ On Heaven’s Door,” the only moment on this record that makes it worthy of mention. But I’ll still take “The Man In Me.” – Casey Burke
Rating: 5.9
Listen/Buy: Spotify | Amazon (vinyl)
Dylan (1973)
Of Bob Dylan’s 39 studio albums, about a half-dozen of them heavily or exclusively comprise covers, including his the critical and commercial flop Self-Portrait, his 2009 holiday album Christmas in the Heart, and his series of standards-driven albums in the 2010s. Dylan is another such release, one made without any input from Dylan himself. Columbia Records compiled the nine covers on the album and released it on their own after Dylan struck up a new partnership with Asylum Records. It’s literally a collection of leftovers and it sounds like it, but without the rowdy looseness of a collection like The Basement Tapes. In principle, this is an album that doesn’t feel like it should exist simply on the basis of reinforcing the worst stereotypes of record label greed, but the material itself mostly isn’t even worth salvaging. He sounds too checked out to bother on his cover of Joni Mitchell’s “Big Yellow Taxi,” while overwrought backing vocals drown out “Sarah Jane” and “Mary Ann.” It’s charming enough to hear his cover of Elvis’ “Can’t Help Falling in Love,” and there’s a rock ‘n’ roll swagger to “A Fool Such As I,” but this haphazardly released collection by its nature ends up being a mess, and the whiplash between his signature singing style and Nashville Skyline croon only reinforces the lack of cohesion or care that went into it. – Jeff Terich
Rating: 4.0
Listen: Spotify
Planet Waves (1974)
Although The Band had been his live backing band (on and off) for some years, Planet Waves was the first studio album on which they backed Dylan, and they knock out quite a few tunes that were jaunty and toe-tapping on this album. It blends strong songs like “On a Night Like This,” “You Angel You,” “Something There Is About You,” and the fast version of “Forever Young” with a lot of filler like “Going, Going, Gone,” “Tough Mama,” “Wedding Song,” and “Hazel,” which is plodding and directionless. An inconsistent album, then, and one which will perhaps always live in the shadow of the justifiably revered Blood on the Tracks which followed it, but one that nevertheless offered up its share of enjoyable moments. – Greg Hyde
Rating: 7.0
Listen/Buy: Spotify | Rough Trade (vinyl)
Blood on the Tracks (1975)
Better writers, thinkers, and musicologists than me have sung the praises of this album for the last 50 years. Whole books have been written about Blood on the Tracks, from its creation myths and recording processes to the various interpretations of the subject matter. While Dylan himself disavows any autobiography, Jakob Dylan has said multiple times these songs sound like his parents talking. Seemingly unheard of today, barely four months elapsed between initial recording and the music hitting record stores, and the songs continue to hit hard. “Tangled Up in Blue” is an immaculate chronicle of lust into love, the lyrics of “You’re Gonna Make Me Lonesome When You Go” are true to its title, “Meet Me in the Morning” is a heartbroken paean to a lost love, and “Shelter from the Storm” serves as a contemporary troubadour’s lament. This album rips. – Adam P. Newton
Rating: 10
Listen/Buy: Spotify | Turntable Lab (vinyl)
The Basement Tapes (1975)
There are a few perfections of American culture; of them, blues, country, roots rock and jazz are among the very greatest. While inestimable words could be spilled about the complete tapes and the hundred plus songs effect on pop culture as dozens of bands recorded and spread them, this document alone underscores two very important points: first, that the Band is perhaps the most underrated rock band of all despite their existing ravenous acclaim and second, that Dylan’s knack for writing in this world justifies why he turned to this sort of music and half a century later hasn’t looked back. This is something beautiful, so beautiful it nearly justifies the project of America. – Langdon Hickman
Rating: 10
Listen: Spotify
Desire (1976)
Desire occupies a strange place in the Bob Dylan catalog. It’s a relative high, but one from a decade containing some of his absolute peaks and most banal lows. So it always felt inconsistent to me. The highs are sometimes Himalayan, like “Isis” with its slinky piano blues, the surreal melancholy of “One More Cup of Coffee,” the forthright moral outrage of “Hurricane,” and the wrenching outpouring of love on “Sara.” There are also excellent sounding trifles like “Black Diamond Bay” or Mozambique” … and then dreck like “Joey.” It’s 11 snail-paced minutes of listless verses, as completely full of shit about Crazy Joe Gallo as “Hurricane” is (mostly) accurate about Rubin Carter’s wrongful (ultimately overturned) murder conviction. But it’s not forgettable—arguably it’s one of his more musically interesting albums. With Scarlet Rivera’s violin having the strongest presence of any instrument and Dylan attempting more trickery with his voice than ever before, Desire is almost a blueprint for freak-folk. – L.D. Flowers
Rating: 7.9
Listen/Buy: Spotify | Amazon (vinyl)
Street-Legal (1978)
Maybe I’m reading too much into things here, but Dylan declaring that he has a pony named Lucifer feels curiously like foreshadowing of the trio of Christian albums he’d release in the next three years. That being said, the last record Dylan released before his turn-of-the-decade religious awakening offers little other indication of what would happen next; if anything, it seems to suggest an alternate path of Springsteen-like heartland rock that, at least here, seemed fertile ground for exploration. Though Street-Legal‘s reputation suffered for a while due to its mix, it’s since been reappraised as one of Dylan’s most underrated albums, and for good reason. Though it’s perhaps less stylistically bold as its predecessor or as affecting and ambitious as Blood on the Tracks, Street-Legal nonetheless is rich in great songs, including “Changing of the Guards” and “Señor (Tales of Yankee Power)”, each one deserving of its place in the Dylan canon, while the liberal use of saxophone and Hammond organ gives the album overall a soulful presence. And if the juxtaposition of this album’s score next to the previous one seems a bit off, well, this album doesn’t include “Joey.” – Jeff Terich
Rating: 8.5
Listen/Buy: Spotify | Amazon (vinyl)
Slow Train Coming (1979)
If I were a different sort of music critic, I would have long ago written a book exclusively about Bob Dylan’s so-called “Christian Trilogy,” the three-album arc he released after his conversion to evangelical Christianity in the late 1970s. Slow Train Coming came first in August of 1979, and it’s much better than you probably remember. Across nine songs in 46 minutes, Dylan delivers high-end folk rock sprinkled with psych, blues, and soul. While this album will never be counted among his best—since it contains some predictably annoying Christian bromides—it deserves more attention because it features three underappreciated classics: “Gotta Serve Somebody,” “Slow Train,” and “Man Gave Names to All the Animals.” – Adam P. Newton
Rating: 7.6
Listen/Buy: Spotify | Amazon (vinyl)
Saved (1980)
The second record of one of Dylan’s few genuinely underrated periods, Saved mines the same fertile ground to diminishing but still peasant reward. This is gospel and country rock, just as it promises on the tin, but the lyrics are as marble-mouthed as ever, so the conceit largely exists seemingly to motivate the tone of the songs rather than compel the listener. And the results are clearly passionate, a component which is necessary for music of this sort, which needs to flow from the heart as much as the hands. Is it on par with his all-time greats? Not really, but if you remember being told it’s a stinker, you owe yourself a revisit. – Langdon Hickman
Rating: 6.7
Listen/Buy: Spotify | Amazon (vinyl)
Shot of Love (1981)
The most frustrating thing about Shot of Love, the third and final album in Dylan’s born-again trilogy, is that you can see very clearly how a decent enough album could have been a much better one. The opening title track is far from his most lyrically profound, but lord does it kick ass. And “Every Grain of Sand,” the gorgeous closing track, ranks alongside “Gotta Serve Somebody” as one of the best things to come from this curiously pious period of his career. The problem, despite so many elements that work, is that in spite of these few examples, nearly every song falls far short of being as strong as it seemingly could have been. Sometimes Dylan’s newfound faith gets in his way, like on the way-too-defensive “Property of Jesus” or the judgy “Trouble.” Sometimes the music is drab (“Heart of Mine”) or a reggae misfire (“Dead Man, Dead Man”). I can roll with Dylan’s Christian reinvention when he’s firing on all cylinders, less so when his proselytizing becomes hectoring, but least of all when even he doesn’t sound convinced. That the potential best song here, the rollicking roadhouse blues of “The Groom’s Still Waiting at the Altar”—which swings like the most fluid moments of Dylan’s Daniel Lanois-produced albums—was initially left off the album is all you need to know about how poorly calibrated his instincts were at the time. – Jeff Terich
Rating: 5.6
Listen: Spotify
Infidels (1983)
Infidels is something of a Rorschach test for Dylan fans—it’s either a hidden gem among his otherwise mostly-bad ’80s period, or… well, just another not-so-great album from his worst decade. Kicking off with the intricate lyricism of “Jokerman,” it certainly teases a return to form after the wayward Christian rock of his previous three albums. Likewise, that song finds Dylan joined by the reggae rhythm section of Sly Dunbar and Robbie Shakespeare, which lends extra cred to a reggae exercise that worked exactly once—though he kept trying it to vastly diminishing returns over the decade. And the addition of Mark Knopfler on the album means no shortage of stellar guitar. But as for the rest of the songs? Well, they’re hit or miss. And they miss more often than I like. There’s a reactionary political streak that does it no favors here, like on “Neighborhood Bully,” which has aged incredibly poorly, particularly given the state of Gaza in 2025. And there’s almost a good point about capitalism’s worst effects in “Union Sundown,” but it veers a little too close to a jingoistic statement about American manufacturing. What he didn’t leave behind from his Christian-rock trilogy was a tendency to scrap the best songs of the sessions, in this case “Blind Willie McTell,” which ranks among his best. Mostly, though, Infidels is the bargain bin find most of us know it as, worth a couple bucks if you got it. And it’s always available for a couple bucks. – Jeff Terich
Rating: 6.3
Listen/Buy: Spotify | Amazon (vinyl)
Empire Burlesque (1985)
Empire Burlesque is Dylan’s most uneven album. Nothing in his catalog achieves quite the same balance of professional and amateurish, full-throated and half-assed. For its sonic signature the album clumsily borrows ‘80s production techniques, coasting all the while on unselfconscious momentum before whimpering out on a perfectly unfitting note with the hushed, acoustic “Dark Eyes.” Brilliant songwriting comes in flashes: “Tight Connection to My Heart (Has Anybody Seen My Love)” and “I’ll Remember You” are both peak ‘80s Dylan. Tucked in the middle is “Clean Cut Kid,” his most thoughtful protest song in decades. Otherwise he’s in power ballad mode, with results ranging from great (“Something’s Burning Baby”) to passable (“Emotionally Yours”) to unlistenable (“When the Night Comes Falling From the Sky”). But even in the worst cases, the skeleton of a better Dylan song hides not far beneath the studio dreck. And in the best cases, the studio dreck empowers Dylan to become even more himself. – Casey Burke
Rating: 7.1
Listen: Spotify
Knocked Out Loaded (1986)
I am going to shoot whoever sold Bob Dylan this synthesizer. You may hear about how “Brownsville Girl,” an epic of classic Dylan lyrical form, is the only good song. This isn’t quite true; “Got My Mind Made Up” is exactly the kind of rough rocker you’d hope for with Tom Petty and the Heartbreakers as his backing band. The rest is hot dog ass. How many takes do you think Dylan had to toss out because they were too lively and good? It feels like the thesis of this record was to make Mike Love-led Beach Boys read as geniuses of the arts. There’s even a confounding “Kokomo”-ass reggae tune for some reason. I literally shouted at my stereo at every single song on the first side, a collection of material so awful I could use it to convince the Nobel committee to take the prize back. – Langdon Hickman
Rating: 1.7
Listen: Spotify
Down in the Groove (1988)
A good example of the whole being less than the sum of the parts. Down in the Groove boasts an array of august guest players (Eric Clapton, Mark Knopfler, Steve Jones, Paul Simonon, etc.), but it left listeners and critics and fans disappointed at the time. Though “Had a Dream About You, Baby” and “Ugliest Girl in the World” have an enjoyable catchiness to them, the gospel elements of songs like “Silvio” and the rendition of “Shenandoah” are more like ill-advised experiments. Down in the Groove was then, and remains now, an unfortunate misstep within Dylan’s mixed, if overall groundbreaking, discography. – Greg Hyde
Rating: 5.3
Listen/Buy: Spotify | Rough Trade (vinyl)
Oh Mercy (1989)
Dylan entered the ’80s on the back end of a trio of records made during a conversion to evangelical Christianity, and its aftermath found him curiously even more adrift, even when joined by some of the biggest names in rock music, from Tom Petty to Mark Knopfler. Shaky a decade as it was for him, however, he closed it out on a 14-year high, refinding his muse in the humidity of the Gulf Coast, leading him on a lively chase through haunted corridors and darkly humorous meditations. Working with producer Daniel Lanois after the two were introduced via Bono (Lanois having just co-produced another masterpiece), Dylan conjured a kind of magic that had eluded him for years. Oh Mercy was recorded entirely at night in New Orleans and that’s exactly what it sounds like—raw, alive and eerie, particularly on moments like standouts “The Man in the Long Black Coat” or “What Was It You Wanted.” It’s at times rollicking (“Political World,” “Everything’s Broken”) and at times deeply moving (“Most of the Time”), establishing the perfect balance of both mood and emotion while delivering his strongest set of songs in years. – Jeff Terich
Rating: 9.3
Listen/Buy: Spotify | Amazon (vinyl)
Under the Red Sky (1990)
Just as soon as the ’80s finally giveth, the ’90s taketh away. After the release of Oh Mercy, his strongest album in over a decade, Dylan teamed up with yet another super-team of rock legends—including George Harrison, Al Kooper, Slash, David Crosby and Stevie Ray Vaughan—that despite their best efforts aren’t up to the task of salvaging some of the most baffling output of his career. The nursery-rhyme cadence of many of the lyrics can be explained in part by the dedication to his daughter, and for that reason a song like “Wiggle Wiggle” can be forgiven if not necessarily worth revisiting. But it’s not actually a children’s album, which makes it all the more confusing, so when he keeps on drawing from Mother Goose throughout a set of slick, pleasant and sometimes somber adult-rock songs, it’s more than a little off putting. That it was the follow-up to an actual masterpiece only adds to the frustration. But at least it’s not Knocked Out Loaded, I suppose. – Jeff Terich
Rating: 2.5
Listen: Spotify
Good As I Been to You (1992)
How do you rebound from an overproduced mess of an album like Under the Red Sky? Apparently, if you’re Dylan, the answer is cutting an album of folk and blues songs that in some cases (“Froggie Went A-Courtin”) date back to the 16th century. Abortive sessions with a full band prompted Dylan to re-record with only his guitar and harmonica, to intriguing results. Unlike the 2010s standards albums, you don’t have to be a folk obsessive to enjoy renditions of “Sittin’ on Top of the World,” “Step It Up and Go,” or “Hard Times.” Good As I Been is also a great showcase for Dylan’s underrated fingerpicking, which hits some delirious highs on my personal favorite from this record, “Blackjack Davey.” – L.D. Flowers
Rating: 8.4
Listen/Buy: Spotify | Amazon (vinyl)
World Gone Wrong (1993)
Dylan’s second consecutive album of traditional folk covers, after 1992’s Good As I Been to You, takes a darker, pared down direction. As with its predecessor, only a fervent student of traditional folk could have made it. But if Dylan were only a fervent folk student, the end result might have been stuffy and academic. It’s his supple livewire playing, more than the songs themselves, that makes World Gone Wrong worthy of note. Never a flashy guitarist, here Dylan gets a ton of mileage from relatively simple acoustic techniques, from the percussive propulsion on “Broke Down Engine” to the crude fluidity in the title track’s acoustic turnarounds. It’s not bold enough to be a great Dylan album, but it’s a charming testament to a mind fixated on molding American music to his ends. – Casey Burke
Rating: 6.8
Listen: Spotify
Time Out of Mind (1997)
The Grammy-winning late-’90s triumph of Time Out of Mind feels perhaps slightly less miraculous given the existence of Oh Mercy, the first record that Dylan made with Daniel Lanois. (That the two often butted heads in the studio likewise complicated the odds it would end in triumph.) But Time Out of Mind adds both mournful gravitas and dark sorcery to the equation, taking inspiration from blues records of the 1950s while convening as many as a dozen musicians in a single take, following a feeling instead of a roadmap. And as far as feeling goes, Time Out of Mind is heavy with it, whether it’s the bittersweet look back at a long life lived (“Not Dark Yet”) or a more hopeful pursuit of redemption (“Trying to Get to Heaven”). But there’s a kind of dark to which this array of players is in thrall in highlights like “Cold Irons Bound,” an update of sorts on Dylan’s classic-era epic stemwinders but burning with a dark, hot, bluesy energy, as much a seance as a jam session. Time Out of Mind is a deeply moving album, but it’s more than that, mystical in its presence and awe-inspiring in its scope. – Jeff Terich
Rating: 10
Listen/Buy: Spotify | Amazon (vinyl)
“Love and Theft” (2001)
Old-fashioned, trend-agnostic and a product of lifelong reverence, Love and Theft is Dylan’s first 21st century masterpiece. “Nobody that I know knows as much about American music as Bob Dylan,” said Dylan’s drummer David Kemper. “He has spent so much time trying to understand, and collecting these songs—it was like a never stopping resource.” And indeed, “Love and Theft” is incredibly rich with references (some would argue too rich; Dylan’s decision to lift several lines from the biography Confessions of a Yakuza earned him accusations of plagiarism). But as always, Dylan saves plenty of room to inject his own personalit(ies) into the material. “Mississippi” is a generational country rocker. “Summer Days” and “Cry a While” are percussive gallopers. “Bye and Bye” floats on a gentle organ pulse. Musically and lyrically it’s an unending fountain, the triumphant kickoff to Dylan’s ongoing ride into the sunset on the railways of the past. – Casey Burke
Rating: 9.5
Listen/Buy: Spotify | Amazon (vinyl)
Modern Times (2006)
If you call your album’s first track “Thunder on the Mountain,” it sure as fuck better live up to its name. A rippling electric lead and cymbal fills evoke that very weather phenomenon to start us off. The rest of the song isn’t quite as feverish, but just two tracks later, “Rollin & Tumblin” is (and then some). Times easily stands among the best “elder statesman” Dylan albums, with effective sequencing (mostly blues-rockers alternating with slower but intriguing country-shuffle tunes) and lyrics, often in blues-couplet formats, that range from zany to dead serious to gorgeous. (I’m thinking of “We live, and we die/We know not why/But I’ll be with ya when the deal goes down.”) The record also contains one of Dylan’s strangest and most interesting songs, “Ain’t Talkin.” It’s a revenge tale set to noir-drenched midtempo blues, a reminder that he’s just a phenomenal storyteller. – L.D. Flowers
Rating: 9.1
Listen/Buy: Spotify | Amazon (vinyl)
Together Through Life (2009)
If we can count 1997’s Time Out of Mind as the beginning of Dylan’s late career resurgence, Together Through Life sits firmly at the midpoint of the timeline and reception by fans and critics. Released in 2009, the album overflows with blues swing, horny swagger, and curious whimsy. Musically, it sits at the intersection of Delta blues, Western swing, and Southwestern mystery, as it’s anchored by the deft interplay of accordion, brushed drumming, creeping guitar licks, and weathered vocal rasp. At times, it loses its way in terms of genre tourism, but the album has tremendous high points, especially “If You Ever Go to Houston,” “Jolene,” and “Shake Shake Mama.” – Adam P. Newton
Rating: 7.1
Listen: Spotify
Christmas In the Heart (2009)
Well, why not? In 2009, Dylan had already spent the better part of the preceding 20 years mining and reinvigorating traditional songs across American music, his reverence on full display. Is it so crazy to think that a Bob Dylan Christmas album might be not only un-embarrassing, but genuinely enjoyable to listen to?
What elevates Christmas In the Heart is how strictly Dylan and his band avoid reinventing or winking at the material. They play it straight because, in Dylan’s words, “There wasn’t any other way to play it. These songs are part of my life, just like folk songs. You have to play them straight too.” The results are lively when it counts, cozy and subdued everywhere else. And Dylan’s wisened, amelodic growl feels even more apropos here than on any of his 21st-century albums. Pour some eggnog. Let love permeate. – Casey Burke
Rating: 7.4
Listen/Buy: Spotify | Rough Trade (vinyl)
Tempest (2012)
Tempest features some enjoyable elements, like the rootsy electric guitar-playing on “Narrow Way,” “Pay in Blood,” and the single “Duquesne Whistle,” but at 69 minutes, the album itself and many of the songs on it feel rambling and undisciplined. At points, Dylan’s grizzled-sounding vocals almost veer into self-parody. Lead single “Early Roman Kings” laid bare how obvious and unsubtle the album’s blues influences were, Dylan trying to sound for all the world like he was from Mississippi rather than Minnesota. At the time of its release, Tempest was critically praised as a return to form, but despite some of the highlights here, in hindsight it hasn’t held up as well as many of his other late-career highs. – Greg Hyde
Rating: 6.4
Listen/Buy: Spotify | Amazon (vinyl)
Shadows in the Night (2015)
Bob Dylan has, let’s say, a checkered history with standards and covers—as likely to turn them into embarrassments as classics—but this Frank Sinatra tribute-by-proxy avoids Dylan’s roster of failed thematic experiments. Shadows in the Night takes songs Ol’ Blue Eyes had sung during his career and makes them relentlessly ethereal and yearning, inferring a slow night at the jazz speakeasy or the far-flung honky-tonk. Dylan, his band, and a select orchestra deliver gloomy, reserved tunefulness on relative Sinatra hits like “Autumn Leaves” and deep cuts like Irving Berlin’s “What’ll I Do,” and by grinding out 10 songs in just 35 minutes they leave the music no time to feel self-indulgent. Marked by echoing production, Donnie Herron’s achingly slow pedal steel, and almost no percussion to speak of, it feels like what might have happened had David Lynch or Quentin Tarantino centered one of their neo-noir film soundtracks around a single artist. Shadows in the Night isn’t in the folk-rock troubadour wheelhouse of many fans, but if you’re in a particular mood or appreciate certain musical atmospheres, this is an absolute breeze to listen to. – Adam Blyweiss
Rating: 8.2
Listen/Buy: Spotify | Amazon (vinyl)
Fallen Angels (2016)
Holy fuck is this album sleepy. It unfolds at a soporific slow-dance pace that can’t be attributed to the era of music it’s covering. This is obviously Dylan’s choice. It doesn’t really pick up at all until “All or Nothing at All,” and just barely. Now … is it bad? Not exactly. Longtime session hands like guitarist Charlie Sexton and bassist Tony Garnier (along with jazz guitarist Dean Parks, the Type of Guy You Get For This Sort of Sound) help Dylan create hyper-competent arrangements. The man tries to mold his voice to the material, and sometimes succeeds. “That Old Black Magic” is honestly a fun track (and thankfully a double-time one). For the most part … what are we doing here? I pity my colleague Langdon Hickman who sat through 96 minutes of this with Triplicate, the final album in Dylan’s standards cycle. – L.D. Flowers
Rating: 5.9
Listen/Buy: Spotify | Amazon (vinyl)
Triplicate (2017)
Thirty songs, even if it’s only about 90 minutes, is a lot of time to have a lot of feelings. I fall in and out of love with this as it plays, grow bored and sentimental, think about my grandmother meeting my grandfather at a USO dance in Connecticut and promising to wait till he came back from the war, think about SpongeBob, think about the hideous floral scent of Florida retirement centers. This kind of project, three discs of pop standards by late-era Dylan, filters every single person it should; Triplicate is absolutely not for everyone and you’ll know if you are one of the few. Were these scattered among originals, arranged in digestible album lengths, everything would be different. These songs are brilliant American Songbook standards played beautifully, recorded even better. An unbelievably fascinating document for absolutely no one but a narrow few. – Langdon Hickman
Rating: 4.3
Listen: Spotify
Rough and Rowdy Ways (2020)
As he approached 60 years of recorded output, academic poetic structures long out of his clutch, Dylan on Rough and Rowdy Ways rests instead on the Beastie Boys formula: simple rhymed couplets, frank and literal surveyances, and endless boasting, all propped up by a laundry list of pop culture references. On its face it’s an awkward cop-out, time drying up his creative juices. But while his nasal, often stumblebum vocals have long been a hurdle for some and a punchline for others, this album finds him somehow embracing a gravelly clarity found in the likes of Nick Cave and Leon Redbone. He’s also surrounded by a crack band reportedly fresh off some of his best touring in years. These elements make arresting his love-song last gasps (“I’ve Made up My Mind to Give Myself to You”), old-time rock ’n’ roll stomps (“Goodbye Jimmy Reed”), and wide range of Bible- and myth-inspired murder balladry (“Crossing the Rubicon,” “Black Rider”). Dylan presents himself here as an aging bluesman grasping for both relevance and standing ovations, seemingly prepping his closing arguments yet unsure if he’ll deliver them to St. Peter, Mephistopheles, or a love of his life. – Adam Blyweiss
Rating: 8.0
Listen/Buy: Spotify | Amazon (vinyl)
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