Well, here we are. I have loved Bob Dylan’s music for a very long time. It was the bedrock of my greatest friendship, the lamp that lights every direction I might venture down. No other musician has shaped my understanding of the world more than Dylan, which makes assembling a list like this all that much harder to do. While he is a hero of mine, there are some duds in his catalog that I almost never revisit. But, for the last two weeks, I’ve been re-listening to every single studio record he’s ever made in order, backwards. And, goodness, what a trial that has been.
Beginning in a place as solid as Rough and Rowdy Ways is a small treasure of spoils, as mining through his various low points—like his Sinatra period, the late-1980s and, of course, his born-again trilogy—is a task fit for only the bravest soldiers. But the riches make it worth it, especially when you listen to everything he made between 1963 and 1969, or what he was doing in the mid-1970s or, most refreshingly, what he was able to achieve in the decade immediately after Time Out of Mind came out in 1997.
For this list, I have excluded an album like Shadow Kingdom—which the internet likes to categorize as a studio LP. But it’s a live record, and I’m keeping it and Before the Flood and Dylan & The Dead and Hard Rain away from the ranking for consistency purposes. Bob Dylan has released 39 new albums in his lifetime, beginning with the self-titled in 1962 and ending with his most-recent effort, Rough and Rowdy Ways, in 2020.
Now, I am fully aware that no two people will agree with this ranking. It is virtually impossible to make a composite list of 39 albums and have every entry slotted in correctly—at least in the eyes of the masses. My goal here was to re-familiarize myself with the catalog of my favorite writer and muse on it. When you get to the Top 15, you can argue for any of the albums being Dylan’s “greatest” and you likely would be right to some degree. In fact, I’m sure my ranking will change tomorrow. And then it’ll change again the day after that. I think that’s the beauty of an artist like Bob Dylan, in that his discography is so expansive that it has something for everyone on any given day. It’s hard to argue with that and it’s even harder to rank, but let’s give it a try. Without further ado, here is every Bob Dylan album ranked from worst to best.
39. Saved (1980)
I’m not against anyone making religious music, but Dylan’s born-again trilogy features some of his, ironically, least-inspired songwriting of his entire career—not to mention the arrangements, which meld rock ‘n’ roll and gospel to a nauseating degree, are too massive to be paired with such unremarkable lyricism. The religious imagery and messages are overwrought and tedious. “In the Garden” and “Solid Rock” are decent enough, and Dylan’s voice sounds pretty good across the album, but Saved is such a misfire that it makes its predecessor, Slow Train Coming, sound like a symphony.
38. Christmas in the Heart (2009)
I’m a Christmas in the Heart hater through and through, but it’s not worse than Saved, that much I can admit. For all of the reasons it’s not good, the album is his first-ever holiday release. And the fact Dylan was 68 when he put it out, no one was expecting it to be a masterpiece. For what it is—a Christmas album—it’s fine. The polka joy of “Must Be Santa” carries the brunt of this record’s appeal, but “Here Comes Santa Claus,” “I’ll Be Home for Christmas” and “Silver Bells” aren’t too shabby, either. This is an album that, even when December rolls around, I never feel too inclined to put on. Sorry, Bob.
37. Empire Burlesque (1985)
While most folks can agree that Empire Burlesque is a bad album, I sometimes feel like I’m in the minority for thinking it’s borderline unlistenable most of the time. Closing track “Dark Eyes” is terrific, there’s no doubt about it. But the nine songs that precede it are just so, so poor. I can’t believe Dylan made Infidels and then pivoted to this. Sigh. “I’ll Remember You” gets better with every listen, though—so Empire Burlesque has that going for it, I guess.
36. Knocked Out Loaded (1986)
Is Knocked Out Loaded the greatest terrible album of all time? The 11-minute epic “Brownsville Girl,” co-written by Sam Shepard, certainly makes a good case for it. If you take that track out of the equation, Knocked Out Loaded could very well be the undoubted, undisputed pick for “worst album made by a great musician”—because, let’s be honest here, there is nothing going on on the other seven songs. It’s a trainwreck, an unsavable disaster. Not even Tom Petty & The Heartbreakers playing on this album could give it enough legs.
35. Good as I Been to You (1992)
Good as I Been to You has the pleasure of being the album that Dylan sounds the worst on, vocally, and it’s not even close, to be honest. While it was a return-to-form folk record, Good as I Been to You sounds like the greatest musician of the 20th century finally feeling unconfident in his own craft. “Jim Jones” and “Hard Times” are solid highlights, but much of this record is a slog that doesn’t stand up well even against the most middle-of-the-road Bob Dylan projects.
34. Under the Red Sky (1990)
If I was ranking these albums based on personnel only, Under the Red Sky would skyrocket up this list—as musicians like Bruce Hornsby, George Harrison, David Crosby, Elton John and Slash make guest appearances. But, plainly put, Under the Red Sky was an underwhelming follow-up to Oh Mercy that saw Dylan retreat to a creative place that would put him in a lackluster lull for seven years. “Born in Time” and the title track are fine, and “Cat’s in the Well” is a fun tune to spend three minutes with, but not even an all-star lineup of players could mask the uninspired blemishes of Under the Red Sky.
33. Triplicate (2017)
The last of a trio of records Dylan put out in three year’s time, Triplicate is a mammoth 30-song homage to covering excerpts from The Great American Songbook. You can imagine how tiring the schtick was by this point, as fans had been without an album of original material since 2012. While much of Triplicate is filler that finds Dylan remarkably uninterested in challenging his own talents, songs like “September of My Years,” “This Nearly Was Mine” and “Somewhere Along the Way” are charming crooner gems that do, very punctually, emphasize the performative magic he still has radiating within him.
32. Pat Garrett & Billy the Kid (1973)
It’s hard to give Pat Garrett & Billy the Kid a fair shake on this list because it is a soundtrack composition. Featuring original recordings and score arrangements, the album is barely an album so much as it’s a documentation of Dylan’s musical work on the film of the same name. But, one crucial element that is present here is that the album features “Knockin’ on Heaven’s Door,” one of Dylan’s most popular songs ever. I do like tracks like “Billy 1” and “Main Title Theme (Billy),” but most of this record is Western instrumental filler. For that reason, it’s largely unlistenable in a casual sense but, again, “Knockin’ on Heaven’s Door” is working overtime here.
31. Down in the Groove (1988)
I think I’m a bit softer on Down in the Groove than most people are, and that is largely because I try not to let its successor—Oh Mercy—overshadow it entirely. Not nearly as bad as Knocked Out Loaded, Down in the Groove finds Dylan working with folks like Eric Clapton, Jerry Garcia and Bob Weir, Mark Knopfler, Mick Taylor and Ronnie Wood. It’s a highly collaborative album that is obviously, at times, inspired by the touring that Dylan was doing with the Grateful Dead around the same time—and a song like “Silvio” all but confirms that truth. The rest of the tracklist is a bit of a slog, but I wouldn’t consider the album to be the rock bottom abomination it has been labeled over the years. The one-take sound of Down in the Groove was not remarkable, but Dylan has done far worse than this.
30. Together Through Life (2009)
“Beyond Here Lies Nothin’” is a great opening track. Beyond that, Together Through Life is a very middle-of-the-road Bob Dylan album. “If You Ever Go to Houston” and “I Feel a Change Comin’ On” hold their own, but songs like “Jolene,” “Shake Shake Mama” and “Life Is Hard” are among some of the most tepid, uninspired original material Dylan has produced since Time Out of Mind. Putting this and Christmas in the Heart out back to back in 2009 would be a death knell for any other musician. But, of course, this is Dylan we’re talking about.
29. Fallen Angels (2016)
For a moment, it seemed like Shadows in the Night was going to be a one-off affair for Dylan in 2015. How could we be so foolish to assume such a blunder? Fallen Angels arrived a year later and felt like a batch of songs that missed its predecessor’s final cut. But, truth be told, it all blends together at the end of the day. 54 years after putting out his debut album, Dylan’s infatuation with Sinatra isn’t the drastic left-turn it might seem like in retrospect. He’s always flaunted his own admiration for the craft of musicality, and Fallen Angels is another example of that—catalyzed by “Melancholy Mood,” one of Dylan’s strongest performances of the last decade.
28. Dylan (1973)
This is the moment where I come out of the woodwork as a proponent of Dylan, a record largely considered to be one of Bob’s most forgettable projects. And, look, I get it. It’s nothing but cover songs left over from the Self Portrait and New Morning sessions and, yes, it’s a mess. But it’s a lovable mess that I return to more often than the rest of the bottom-of-the-barrel albums. I’m particularly keen on his cover of Jerry Jeff Walker’s “Mr. Bojangles,” and his take on Joni Mitchell’s “Big Yellow Taxi” is fun and loose. Listen to Knocked Out Loaded and you’ll be wishing you were listening to Dylan instead.
27. Shot of Love (1981)
I don’t think Shot of Love is necessarily a good album, but it is an over-hated album. It’s definitely the best of the born-again trilogy—which I realize is not saying much—and that is mostly due to the last track, “Every Grain of Sand.” A recurring theme here is that, above all else, Bob Dylan is pretty damn good at putting an incredible song at the end of his worst albums. Much respect to a man who knows how to close things out on a strong note. But other than “Every Grain of Sand,” I rarely revisit any of Shot of Love, though I do like the title track a decent amount—which is likely because of Carolyn Dennis’ background vocals.
26. Shadows in the Night (2015)
Shadows in the Night was the first “new” Dylan album I ever bought with my own money, and it came out right around the time I was having my own Sinatra phase. He cut the record in Capitol Records’ Studio B with a five-piece band and a small orchestra, and he relished using the tools he’d sharpened on Tempest for the greatest good. These standard covers, especially “The Night We Called It a Day,” “Stay With Me” and “That Lucky Old Sun,” are relatively great. Out of all of the late-career moves made by our most important rock stars, Dylan’s pivot towards his own grasp at Sinatra’s oeuvre was a unique and welcomed one—even if he did, when it was all said and done, milk it a little too much.
25. World Gone Wrong (1993)
The last breath of the Dark Ages in Dylan’s canon, World Gone Wrong is one of the sharper entries to listen to. It won a Grammy for Best Traditional Folk Album, despite its glaring lack of originality. Dylan was trying to resurrect himself as a folk singer, so he covered songs by bluesmen, like Willie Brown’s “Ragged & Dirty” and Blind Willie McTell’s “Broke Down Engine.” The record was not a blemish like Good as I Been to You, but it wasn’t a soaring success like Time Out of Mind, either. Songs like “Blood In My Eyes” and “Lone Pilgrim” are these weird and haunting and surrealistic tunes that, if only for a brief moment, make us remember the Bob Dylan who stole our hearts in the first place.
24. Slow Train Coming (1979)
Slow Train Coming would be closer to Saved territory if it weren’t for its opening song “Gotta Serve Somebody.” Yes, the album did win Dylan a Grammy for Best Male Rock Vocal Performance, but it kicks off the born-again trilogy in a rather lackluster way. What is working for it, though, is that it 1) sounds good and 2) Dylan’s lyricism and singing are both still worth writing home about. Maybe more important than anything else, however, is that the religious messages Dylan is trying to convey on songs like “Precious Angel,” “Gonna Change My Way of Thinking” and “When He Returns” aren’t overwrought to the point that they diminish the sonic quality of the album, which features great guitar work from Mark Knopfler—which I’ll never complain about.
23. Bob Dylan (1962)
Bob Dylan’s self-titled album barely helped the songwriter gain any traction, at least not at first. Released in 1962, it featured some of Dylan’s more recognizable songs—like “Song to Woody,” “Baby, Let Me Follow You Down” and, most especially, “Man of Constant Sorrow.” He only wrote two original songs on the album (“Talkin’ New York” and “Song to Woody”), but he arranged three others and pulled cues from Eric Von Schmidt and Dave Van Ronk elsewhere. Bob Dylan is a good folk record that is a good place to look if you want to see the greatest storyteller of all time before he was ever labeled as such. From a quality standpoint, it’s all there—and you can hear Dylan perfecting his disaffected yet nuanced delivery in real time.
22. Planet Waves (1974)
Dylan’s last album with Asylum Records, Planet Waves is the epitome of a middle-of-the-road album, in my opinion. Its highs outweigh its lows, and much of that is thanks to The Band backing him up on these songs. The two-part “Forever Young,” which is broken up into a slow version and a fast version, remains one of the most celebrated compositions in Dylan’s entire catalog, but tracks like “On a Night Like This,” “Going, Going, Gone” and “Never Say Goodbye” are equally as moving and exciting—particularly the latter, which features Robbie Robertson absolutely shredding on the guitar. You can rarely go wrong with a formula like that. If only they’d plugged that in for the rest of the record, too.
21. Tempest (2012)
The most underrated post-Time Out of Mind album in Dylan’s catalog, this is where he really foreshadowed his eventual turn towards pop, jazz and R&B standards. On tracks like “Duquesne Whistle,” “Soon After Midnight” and “Pay In Blood,” he flexes his songwriting chops with scatting poetry while delivering bellowing, gravelly vocals in the process. At 71 years old, Dylan sounded remarkably confident on Tempest, putting color into dust-covered musings. “I ain’t dead yet, my bell still rings,” he lets out on “Early Roman Kings,” which is a matter of fact you can’t argue with. The 14-minute title track is of Dylan’s best performances from the last 15 years, as he weaves through 45 verses riffing on the Titanic, Leonardo DiCaprio. Tempest is a web of mortality, hope and worry spun gracefully.
20. Self Portrait (1970)
I can’t really pinpoint why, but I am unabashedly pro-Self Portrait. I won’t go as far as saying it’s a misunderstood album or anything like that, because it’s really not. Everyone who has a bad opinion about this record is correct, but everyone who loves it dearly is also correct. The negative reactions haven’t softened up over the years, and it’s been considered a widely lackluster “end” to Dylan’s tenure as a “spokesman of a generation.” Nevertheless, this album is, somehow, a gift that keeps on giving. It pairs the country vocal affectation Dylan used on Nashville Skyline with the messiness of a man who is uncertain about his own creative direction. A song like “Alberta #1” is deftly beautiful, as is “Wigwam” and “The Mighty Quinn (Quinn the Eskimo).” The live take on “Like a Rolling Stone” is sublime enough, and I actually really, really love Dylan’s cover of Simon & Garfunkel’s “The Boxer.” I’m not going to shout from the rooftops that Self Portrait is some magnum opus or anything of the sort, but it’s a really great and chaotic record I return to often.
19. John Wesley Harding (1967)
The first entry in the “really good” tier of this list, John Wesley Harding is a stellar album overshadowed by the magnitude of the collective magnitude of the three albums that preceded it. The record was made around the same time as The Basement Tapes sessions, and it produced a few of Dylan’s most crucial compositions: “All Along the Watchtower” and “I’ll Be Your Baby Tonight.” While psychedelia was dominating the zeitgeist, Dylan had no interest in contributing to or critiquing it at all—and that is, perhaps, what sets the album back. Dylan was always at the forefront of commentary, but John Wesley Harding basks in its own lore and thrives on its own confidence. It’s not a front-to-back classic like Blonde on Blonde or Highway 61 Revisited, but it bridges the gap between Dylan’s electric period and his forthcoming pivot towards country music.
18. Street-Legal (1978)
In my time as a Dylan student, no album has grown on me more than Street-Legal, which just so happens to boast one of his greatest songs ever, “Changing of the Guards.” I don’t care what anyone says, it’s a Top 5 song in his catalog, and it completely prevents the rest of the album from cap-sizing under the weight of its own muddied production. But elsewhere, “Baby, Stop Crying,” “True Love Tends to Forget” and “Where Are You Tonight? (Journey Through Dark Heat)” are standouts, too. Steve Douglas steps in and lays down some incomparable sax work all across Street-Legal, and we get more vocals from Carolyn Dennis here. The pieces are present, and Dylan somewhat makes them all fit together well enough. I tend to side with the re-appraisals of this album, though I’m sure the forthcoming born-again trilogy does heighten my appreciation for Street-Legal to an extent. Optics are everything, as they say.
17. Another Side of Bob Dylan (1964)
The best part about Another Side of Bob Dylan is that there’s not really a skip on the entire record. It’s just a good collection of 11 really well-written songs. Between “All I Really Want to Do,” “My Back Pages” and “It Ain’t Me Babe,” Dylan made some of the most-covered songs of their era—though they sound pretty incredible in their original format here. Overshadowed by the two albums that came before it, Another Side of Bob Dylan is the final mark in Dylan’s trilogy of protest albums and, unfortunately, just didn’t have any of the knockout punches that its predecessors boasted. It’s still great, though, and worth returning to.
16. Time Out of Mind (1997)
It was the album that reminded the entire world why Bob Dylan is our greatest living songwriter. Time Out of Mind arrived four years after the middling World Gone Wrong and remains one of the greatest course corrections in music history. It’s a comeback record, that much is for sure, and Dylan was rewarded with an Album of the Year Grammy and an immortality now cast in solid gold. He welcomed 12 musicians into the fold, tinkering with a battalion of guitars and organs and producing what was—at the time—his most dynamic and orchestral project yet. And this album is packed to the brim with all-timers, including “Love Sick,” “Not Dark Yet” and “Cold Irons Bound.” A song like “Make You Feel My Love,” in all of its devastating and beautiful glory, has lived a thousand lives on its own, and Time Out of Mind’s 16-minute closer, “Highlands,” was a watershed moment for Dylan. This marks a renaissance that yielded three of the best albums of its era, a recurring theme in Dylan’s long, unimpeachable and unmistakable career.
15. Oh Mercy (1989)
After one of the worst three-album runs any rock legend has ever had, Oh Mercy was a breath of fresh air that, for at least a moment, welcomed the Bob Dylan of old back into the forefront of musical immortality. It was miles and miles better than its predecessor, Down in the Groove, and capped off the worst decade of Dylan’s career with a watershed moment. A comeback record in spirit, Oh Mercy is a triumphant display of songwriting, despite Daniel Lanois’ production, which is so overdone at times that Dylan’s coherent and lucid lyricism is almost washed out. Thankfully, though, he is a titan of the art and cannot be outmuscled by technical misfires. “Everything Is Broken,” “Most of the Time” and “Shooting Star” are catalog cornerstones, and Oh Mercy remains a taut, studded affair.
14. New Morning (1970)
One of my faults as a Dylan fan is my undying allegiance to New Morning. I think this album is much better than the credit it gets, and it boasts three of the very best songs the man ever wrote: “If Not For You,” “Sign on the Window” and “The Man in Me,” the latter of which receiving a second life thanks to The Big Lebowski. But New Morning looks awfully good standing next to Self Portrait, and it looks even better standing next to Planet Waves and Dylan. And yet, the lackluster quality of every record around it doesn’t oversaturate its own triumphs. Dylan is working through the same country rock arrangements he perfected on Nashville Skyline, but, this time, he’s welcomed back the nasally singing we all adore. His piano-playing is stellar, especially on a masterpiece like “Sign on the Window,” which is so often overlooked in the pantheon of Dylan’s oeuvre that it very well might be the most underrated song he’s ever released. When New Morning came out, Rolling Stone published a headline that read “WE’VE GOT BOB DYLAN BACK AGAIN!” and they were right.
13. The Times They Are a-Changin’ (1964)
I made a tweet a while back claiming that The Times They Are a-Changin’ is Bob Dylan’s best album. Now, I’m not necessarily walking that statement back, but I am also a sensible person and wouldn’t dare go out on a limb and put it in concrete writing on the website of a major music publication. My reputation is on the line here! But The Times They Are a-Changin’ is one Dylan’s very best albums, and it holds some of the best folks songs ever written—especially the title track, “With God on Our Side,” “Only a Pawn in Their Game” and “The Lonesome Death of Hattie Carroll,” to name a few. As I continue returning to the album, though, I gravitate towards the softer cuts, like “One Too Many Mornings,” “Boots of Spanish Leather” and “When the Ship Comes In.” Given the monolithic legacy of “The Times They Are a-Changin,’ it’s easy to overlook just how all-around great the whole project is. As a follow-up to The Freewheelin’ Bob Dylan, it pales. Look beyond the comparisons, and it succeeds with a storytelling vibrancy Dylan would later ditch for surrealist musings that better suited his disdain for being a “spokesman of a generation.”
12. “Love and Theft” (2001)
The first album Dylan recorded with his Never Ending Tour band, “Love and Theft” continued the momentum of his creative comeback. Most days, I love this record much more than Time Out of Mind, as it sounds like Dylan had fully immersed himself in the new, bluesier direction he was going in. “Love and Theft” is a masterclass missile traveling at a medium pace, as Dylan stretches his wings and delivers methodical, spirited and comprehensive roots songs. “Mississippi” remains one of his sweetest tunes, and “Summer Days,” “High Water (For Charley Patton)” and “Po’ Boy” welcome a varied mirage of sounds and successes into the Dylan pantheon. Inspired by everything from Tin Pan Alley to John Ford to Jack Kerouac, “Love and Theft” was an instant classic upon release and has aged gracefully ever since.
11. Rough and Rowdy Ways (2020)
Around the time Dylan released Rough and Rowdy Ways in 2020, there was an expectation that he would continue on his path of singing jazz and pop standards until the magic ran out. Between 2015 and 2017, he put out more than 50 official studio tracks of that caliber, signaling his brief turn away from original material. But Rough and Rowdy Ways was a surprising return to form, catalyzed by the 17-minute, epic lead single “Murder Most Foul”—written about and around JFK’s assassination in 1963 (and featuring the impeccable “Rub-a-dub-dub, it’s a murder most foul” line). The album was a high point during the genesis of the pandemic, as it welcomed our greatest songwriter back into the echelons of his own craft. Songs like “Key West (Philosopher Pirate),” “False Prophet,” “I Contain Multitudes” and “Goodbye Jimmy Reed” are among some of the best poems Dylan has written this century, and Rough and Rowdy Ways speaks the volumes his catalog had so dearly been missing since, roughly, 2006.
10. Infidels (1983)
Am I putting Infidels too high? No, I’m not. It’s a Top 10 Dylan album and I’ll stand by that proclamation. He put the born-again trilogy away and made one of his prettiest-sounding projects, and thank goodness for that. After releasing Slow Train Coming, Saved and Shot of Love in rapid succession, Dylan took two years off and then returned with one of the most stirring albums about love and loss that he ever wrote. He was singing about the world, the environment and the geopolitics that encompassed all of it. Infidels feels like the perfect marriage of protest singer Bob Dylan and jazz-influenced crooner Bob Dylan—which, to me, is a perfect amalgam; a balm, even. “Jokerman,” “I and I,” “Sweetheart Like You,” “License to Kill”—these are some of Dylan’s all-time best works. My favorite, however, remains the closing track “Don’t Fall Apart on Me Tonight,” a sweet six-minute slice of jangly Heartland rock. With a crew of Alan Clark, Mark Knopfler, Clydie King, Sly Dunbar, Robbie Shakespeare, Mick Taylor and Benmont Tench behind him, Infidels is the crown jewel of Dylan’s third act.
9. The Basement Tapes (1975)
Originally recorded by Dylan between 1967 and 1968 (and later overdubbed in 1975) with The Band (at the time known as The Hawks) after his motorcycle accident in 1966, The Basement Tapes is a rich, loose and animated archival of 76 minutes of raucous music-making between some of the best performers of their generation. The story goes that over 100 songs were recorded during the sessions—including original material, covers and traditional takes—but the 24 entries we get on The Basement Tapes are some of the most inventive musings Dylan ever had a hand in. In hindsight, it’s clear just how crucial these songs were in bridging the eras of Dylan’s career, helping him move on from the poetic, organ-and-electric-guitar rock ‘n’ roll of Highway 61 Revisited and Blonde on Blonde and venture towards the Americana and country stylings that would influence John Wesley Harding and Nashville Skyline. The heavy hitter from the batch is “You Ain’t Goin’ Nowhere,” but songs like “This Wheel’s On Fire,” “Yazzo Street Scandal” and “Goin’ to Acapulco” are incredibly fun moments to revisit.
8. Modern Times (2006)
The general consensus is that Modern Times was the end-cap to Dylan’s Y2K renaissance, and I’m inclined to agree. The album is bulletproof from top to bottom, boasting some of the best songs in Dylan’s late-career period—including “Spirit On the Water,” “Someday Baby” and “Ain’t Talkin’.” It’s a real melting pot of sonics, too, working immensely in the orbits of blues and soul, with some hints of singer/songwriter and piano-folk spotted here and there. Dylan self-produced Modern Times (under the pseudonym “Jack Frost”) and pulled many (uncredited) lyrics from lines in Henry Timrod’s poems. The album scored two Grammys, hit #1 on the Billboard 200 (the first Dylan album to do so in 30 years) and spurred much critical euphoria. It sounds like a crew of players lavishly bouncing off of each other in a studio, making it one of Dylan’s most lived-in albums ever.
7. The Freewheelin’ Bob Dylan (1963)
The album that turned Bob Dylan into a folk hero, The Freewheelin’ Bob Dylan holds up 61 years on—largely thanks to the cultural staying power of “Blowin’ in the Wind.” But when you look past that track, you’ll find some of the sharpest compositions in all of Dylan’s catalog, including “Girl from the North Country,” “A Hard Rain’s a-Gonna Fall” and “Masters of War.” Side two of the album, in particular, is a wondrous place for joyous exploration, as Dylan opens with the greatest breakup song of all time, “Don’t Think Twice, It’s All Right,” and segues into “Bob Dylan’s Dream,” “Oxford Town,” “Talkin’ World War III Blues” and “Corrina, Corrina” in succession. Freewheelin’ changed everything for Dylan, turning him into a titan of his own craft and making him a spokesman for disaffected people here, there and everywhere. The way he wrote about nuclear warfare and the Civil Rights Movement was unlike anything his peers were coming up with, and his moralistic and rebellious juxtapositions was a mark of complexity never before seen in folk music.
6. Highway 61 Revisited (1965)
It’s hard to argue against a record that is responsible for housing one of the greatest rock ‘n’ roll songs of all time, and Highway 61 Revisited kicks off with the six-minute wonder of “Like a Rolling Stone.” But what makes Highway 61 Revisited such an important album is not just its immortal opener. Songs like “Ballad of a Thin Man,” “Queen Jane Approximately” and “Just Like Tom Thumb’s Blues” are bulletproof treasures you’d be a fool to skip during a playback. A tracklist greatly defined by its exorbitant display of organ-playing by Al Kooper and Paul Griffin, Highway 61 Revisited showcased Dylan going fully electric for the first time ever (save for a few numbers), and it christened a new age of rock ‘n’ roll—famously seeing Bob leave his protest singer image behind, exchanging social causes for absurdist, poetic musings that give blues-based rock arrangements a surreal and raucous energy. And then there’s the album’s final song, “Desolation Row,” which—I would argue—is a better encapsulation of Dylan’s greatness than “Like a Rolling Stone.” At 11 minutes and done with an extravagant use of stream-of-consciousness vignettes and biting language, it solidifies Highway 61 Revisited as a masterpiece.
5. Desire (1976)
When I was 18 years old, I would’ve gone the distance arguing that Desire is Bob Dylan’s best album. I’ve softened on that stance in the years since, but I still think it can go toe-to-toe with 90% of his catalog. Beginning with “Hurricane”—which might be his greatest protest song ever—Desire is not as conceptual as its predecessor, Blood on the Tracks. The eight-minute epic about the wrongful imprisonment of boxer Rubin Carter might initially seem like it doesn’t line up with the romantic and absurdist portraits strewn across the rest of the album, but it is a crucial reason why Desire is so brilliant. The album is a character study, the perfect next chapter after the interpersonal brutality of Blood on the Tracks. The 11-minute “Joey” acts as a parallel to “Hurricane,” as it glorifies the life of gangster “Crazy Joey” Gallo. But elsewhere on the record, songs like “One More Cup of Coffee (Valley Below),” “Mozambique,” “Oh Sister” and “Romance in Durango” display fantastical imagery and characters you’d rather read about than hangout with, packed with guest personnel like Emmylou Harris, Eric Clapton and Ronee Blakley. But what makes Desire such a momentous piece of Dylan’s catalog is the stunning finale track, “Sara”—a dashing, heavy-hearted song written about his estrangement from his then-wife Sara Lownds. It’s a canonically important song for Dylan, weaving in Blonde on Blonde motifs while acting as a perfect coda to the disintegrating nuptials at the heart of Blood on the Tracks.
4. Bringing It All Back Home (1965)
Bringing It All Back Home came at the most pivotal point in Dylan’s career. The spotlight usually gets thrown onto Highway 61 Revisited, and I understand why. But Bringing It All Back Home is what bridged the two most important eras of Dylan’s artistry. The first half of the album sports all electric songs, pointing to the songwriter’s new direction. On the flip side, the album’s second half is all acoustic, harkening back to the protest singer world he first cut his teeth in. At the time of its release, Bringing It All Back Home was a divisive project, as it saw Dylan all but abandoning the folk scene that built him up in favor of the heavier instrumentation dominating the culture post-British Invasion. But the record’s significance is imperative and incomparable. “Subterranean Homesick Blues” remains one of the most energetic, off-kilter openers in all of rock ‘n’ roll, while “She Belongs to Me” and “Love Minus Zero/No Limit” are two of the sweetest songs in the Dylan pantheon. Likewise, side two features—what I would argue is—the best four-song run Dylan ever fashioned. Beginning with the kaleidoscopic, literary beauty of “Mr. Tambourine” and culminating with the back-to-back punches of “It’s Alright, Ma (I’m Only Bleeding)” and “It’s All Over Now, Baby Blue,” Bringing It All Back Home is the greatest lyrical outing in all of Bob Dylan’s catalog and, without it, he wouldn’t have been able to make Highway 61 Revisited and Blonde on Blonde. It’s the first chapter in a trilogy of albums that forever changed the sonic course of rock ‘n’ roll.
3. Nashville Skyline (1969)
I truly believe that only Bob Dylan could drop his folk act and make one of the best country albums of all time without really shedding a single ounce of himself. Sure, he trades in his nasally vocal trademark for an affected croon, but it never feels forced—some of that likely due to the fact he quit smoking for a short amount of time. Nashville Skyline is, though, one of the best records of its era and, if it weren’t for Dylan having made three of the most important albums of all time, it would be #1 here. It kicks off with Dylan doing a duet with Johnny Cash on a reimagined version of “Girl from the North Country,” only to segue into a string of beautiful tunes like “To Be Alone With You” and “I Threw It All Away.” The quirkiness of “Peggy Day” and “Country Pie” sometimes get overshadowed by the talismanic, gravitational staying power of album centerpiece “Lay Lady Lay,” but the real bread-winners of Nashville Skyline are “Tell Me That It Isn’t True” and “Tonight I’ll Be Staying Here With You.” From start to finish, Nashville Skyline is a perfect no-skip record that boasts one-dimensional song structures, sharp lyricism and shoots from the hip. It sounds like a victory lap, and it certainly was one.
2. Blonde on Blonde (1966)
For a long time, Blonde on Blonde would have been my no-doubt-about-it pick for #1. I mean, it’s the greatest double album ever made, after all. Recorded in New York Ciy and Nashville across three months in 1966, Blonde on Blonde took Dylan’s modernist poetics and merged them full-on with the electric blues and folk rock he’d so poignantly fleshed out in the year prior. The true mark of our greatest lyrical visionary, Blonde on Blonde is massive in scale and execution, as songs like “One of Us Must Know (Sooner or Later),” “Visions of Johanna,” “Just Like a Woman” and “I Want You” are among the most important in the Dylan pantheon. Even the more underrated tracks, like “Fourth Time Around” and “Pledging My Time,” are stunning in their brilliance. You can see, from “Rainy Day Women #12 & 35” all the way down to “Sad-Eyed Lady of the Lowlands,” that Dylan was at the height of his powers in every sense of the term. And “Sad-Eyed Lady of the Lowlands,” I will go to my grave contending that it is, without a doubt, the greatest song Bob Dylan has ever penned. At 11 minutes in length, it takes up all of side four by itself and fleshes out an entire colloquial ecosystem across its runtime. Blonde on Blonde should be credited with re-inventing the language of rock ‘n’ roll, as it remains miraculously taut and marvelously triumphant.
1. Blood on the Tracks (1975)
While it’s not a shocking pick to make, there is no doubting that Blood on the Tracks is not just Bob Dylan’s greatest album, but one of the single greatest records in the history of modern music as we know it, too. While Dylan has long denied that Blood on the Tracks is an autobiographical album, it’s widely assumed that the 10 songs are greatly inspired by his estrangement from his then-wife Sara Lownds. What is true, no matter what, is that the album is a perfect breakup story that really gnaws away at the brutality of interpersonal grief and the anger, loss and vindictiveness that arises between two people who love each other but can’t keep growing together. “Tangled Up in Blue” is one of Dylan’s greatest songs ever, while “Simple Twist of Fate,” “Shelter from the Storm” and “Buckets of Rain” are cornerstones in his catalog. But when I revisit Blood on the Tracks, I immediately retreat to the singularity of “Idiot Wind” and “If You See Her, Say Hello,” two of Dylan’s finest lyrical outings that are often underscored by the more palatable and immediately devastating folk tunes on the album. After a string of so-so outings between 1970 and 1974 that didn’t move the needle much on his legacy, Blood on the Tracks was a welcomed return to form for Dylan—an album that cemented him, likely for good, as the greatest songwriter ever. No musician produced a narrative as sharp and devastating before Blood on the Tracks came out, and no one has come close since.