On May 24, Bob Dylan turns 80.
I can’t overstate how grateful I am that he’s still with us. Bob Dylan is my favorite artist ever. He’s also my favorite singer, songwriter (or writer of any kind, really), rock star, harmonica player, set of personas, occasional avant-garde film director, mostly silent western film actor, wide-brimmed hat enthusiast, and, well, I could go on forever. Let’s just say that his work means a lot to me. I’ve spent countless hours listening to and thinking about this man, and my interest in him has only grown over the years. Bob Dylan truly is a bottomless well. Take a drink, and you’ll remain thirsty your whole life.
In celebration of Bob’s upcoming birthday, I’ve decided to undertake an irresistible but dangerous proposition for a Dylan obsessive: I’m going to rank all of his studio albums. Originally, I thought about doing all of his albums, including live records and installments of his essential Bootleg Series. But I realized that this might very well kill me, or at the very least cause my wife sneak off in the night with the kids. So! I’m sticking just with the studio albums.
How does it feel … to be on your own … like a person ranking Bob Dylan studio albums? Come with me on this journey through dark heat. Be sure to grab one more cup of coffee before we go to the valley below, because this is going to take a while.
39. Knocked Out Loaded (1986)
I love every Bob Dylan album, even the bad ones.
Here’s what I love about Knocked Out Loaded: There’s “Brownsville Girl,” the epic ramble where Bob (with assistance from playwright Sam Shepard) tries to remember the plot of the 1950 Gregory Peck western The Gunfighter and then wanders off on an 11-minute tangent about chasing a woman through southern Texas. There’s also this description of mid-1980s Bob courtesy of Mikal Gilmore in a 1986 Rolling Stone cover story: “It is just past midnight, and Dylan is standing in the middle of a crowded, smoke-laden recording studio tucked deep into the remote reaches of Topanga Canyon. He is wearing brown-tinted sunglasses, a sleeveless white T-shirt, black vest, black jeans, frayed black motorcycle boots and fingerless black motorcycle gloves, and he puffs hard at a Kool while bobbing his head rhythmically to the colossal blues shuffle that is thundering from the speakers above his head.”
Here’s what I don’t love about Knocked Out Loaded: The badassery of that description hardly ever carries over to the actual album. According to Gilmore, Dylan at this time was “turning out spur-of-the-moment, blues-infused rock ‘n’ roll with a startling force and imagination.” And yet when he put together this album, he ultimately retreated into confusion and defeat. The album is an amalgam of misbegotten overdubs — the synth and drums sounds are terrible even for the era — and indifferent performances culled from various sessions scattered over several years. Or, as Dylan put it to Gilmore, “It’s all sorts of stuff. It doesn’t really have a theme or a purpose.” Even “Brownsville Girl,” the one song from Knocked Out Loaded most people agree is good, is diminished where you hear the superior earlier version that didn’t make the record. Let’s just say the title isn’t ironic.
38. Christmas In The Heart (2009)
If I can correct something I just wrote — what could be more Dylanesque than doubling back and contradicting yourself? — I typically refrain from labeling any Bob Dylan album as “bad.” Because I know that Bob is always ahead of me.
In the past, I have made the mistake of calling a particular Dylan album “bad” in public, only to realize five to ten years later that said album has grown on me to the point of it now being one of my favorites. There are numerous instances of this phenomenon further down on this list. By now I have learned my lesson: If you make a negative judgment about Bob Dylan, he will prove you wrong somewhere down the line.
Therefore, I am willing to preemptively concede that Christmas In The Heart — an album that made zero sense to me when it came out in 2009, and to my delight still confounds me a dozen years later — is probably a work of genius that I just haven’t been able to wrap my feeble mind around quite yet. As a pea-brained normie, Christmas In The Heart initially seemed like a goof, especially the loopy music video for “Must Be Santa” in which Bob bounces merrily around a raucous holiday party in a lopsided blonde wig that makes him look like Val Kilmer’s character in Heat dressed as Val Kilmer’s character in Tombstone.
But now, it’s clear that this old-fashioned evocation of pre-rock (and borderline corny) Americana is actually an important signpost indicating the direction he was about to take in the 2010s. In another 12 years, we might eventually realize that Christmas In The Heart is a turning point in the overall direction of popular music. Stay tuned.
37. Triplicate (2017)
36. Fallen Angels (2016)
35. Shadows In The Night (2015)
In 2012, Dylan gave perhaps the most jaw-dropping interview of his career to Mikal Gilmore (who truly is the Bob whisperer). At the most incredible moment of this incredible conversation, Bob takes out a book about Hells Angel Sonny Barger and points to a page describing the death in the early ’60s of a young motorcycle-riding man named Bobby Zimmerman. For Bob, this is highly significant. He starts talking about transfiguration, implying a link between himself, this long-dead kid, and the book’s co-authors, who also happen to have the last name Zimmerman.
Gilmore, understandably, is confused. Is Bob saying that kid is somehow a prior version of himself? Is he comparing this kid’s accident to the mythology surrounding his own motorcycle accident around the time of Blonde On Blonde‘s release? These are logical questions! But Bob is annoyed by them. To him, his point about Sonny Barger and this other Bobby Zimmerman and the act of a human form suddenly taking on a mystical, spiritual shape is perfectly obvious.
I am sure that Bob would also be annoyed if he somehow read this list and learned that his decision to record three albums — including one triple record — of classic American songs is perceived by at least one self-described hardcore Dylan fan as a head-scratching indulgence. I get making one album in this vein, and I would have been fine if Strangers In The Night had been that one album. It’s a perfectly lovely piece of music that immediately sets a mood of creamy melancholy and then doesn’t deviate from it at all. But releasing another 40 (!) songs with that same mood and sound is a bit much.
Again, I know Bob is ahead of me, so I will probably love all three of these albums down the road. And I appreciate how singing these songs set him up for his tremendous vocal performance on Rough And Rowdy Ways. But beyond that, I’m still pretty lost with Bob’s “slow-core Rod Stewart” period.
But then I go back to the whole transfiguration thing. And I remember a line from the song “Bob Dylan’s Blues” that Bob spoke-sang in 1962:
Unlike most of the songs nowadays that have been written up in Tin Pan Alley
That’s where most of the folk songs come from nowadays
This, this is a song, this wasn’t written up there
This was written somewhere down in the United States
Like most of us, Bob Dylan learned to embrace as an old man what he mocked as a young man. Or maybe the kid Bobby Zimmerman who sang that simply died in a motorcycle accident many, many years ago.
34. Under The Red Sky (1990)
Almost nobody likes this record. Dylan himself thought for a spell that it might be his final album, describing the process of recording at the time as “too mental.” This is a curious comment, given that Under The Red Sky is Dylan’s at his unadulterated dumbest. Many of the lyrics sound like nursery rhymes. (From the title track: “Let the wind blow low, let the wind blow high / One day the little boy and the little girl were both baked in a pie.”) At least one Dylanologist, Patrick Humphries, attributes this to Dylan becoming a father for the sixth time a few years before the album was made. In which case, I hope his child enjoyed “Wiggle Wiggle.”
Because this is Bob Dylan, however, even Under The Red Sky has some high-profile fans, including the most committed Dylan critic and biographer, Clinton Heylin, who claims it’s as good as the album that precedes it, 1989’s Oh Mercy. Robert Christgau went even further, calling it his best album in 15 years. (Essentially the “his best since Blood On The Tracks” compliment that became a late-era Dylan cliché.) On one hand, these seem like crazy assertions. On the other hand, I love every Bob Dylan album, even the bad ones. These guys might be on to something.
Either way, this record is the sort of charming abomination that only a genius can make. Under The Red Sky finds Dylan at his absolute lowest, where he’s literally saying, “I don’t know how to make records anymore.” And it’s still … pretty listenable. I personally like the idea of Bob playing with Slash, David Crosby, and George Harrison on a bunch of songs that sound like “Knick Knack Patty Whack.” Bless this mess.
33. Down In The Groove (1988)
The liner notes of this record are a masterpiece. Eric Clapton and Kip Winger play on the same song. Half of the Grateful Dead sing on a different song. (I say this with love as a Deadhead: Singing was not the Grateful Dead’s strength in the late ’80s.) On another track, Steve Jones of the Sex Pistols and Paul Simonon of The Clash team up for a one-off punk supergroup, and all you can hear is a cheesy organ lick that sounds like an early Clinic record. American Idol judge Randy Jackson is a significant figure on two other numbers. The result is hardly classic Dylan. When he sings “Death Is Not The End,” you sense his disappointment.
Not even Robert Christgau defends Down In The Groove. (He called it “horrendous product.”) But this is my favorite Dylan trainwreck. Every Dylan fan has the right to overpraise one widely dismissed clunker, and I’m spending my capital on this poorly treated runt of the litter.
If “silly, ramshackle, and incoherent Dylan” is a virtue, it doesn’t get more virtuous than this record. Over the years, I’ve warmed to its sloppiness, which I prefer to the more processed sound of many of Dylan’s ’80s records. And the strange combination of musicians sometimes stumble into fascinating accidents, like the synth-y cover of Big Bill Bronzy’s “When Did You Leave Heaven?” that is the best War On Drugs song of 1988.
32. Together Through Life (2009)
Bob Dylan collected guitar players in the ’80s like Neil Young hoarded vocoders. And he sometimes reverted to this habit in later decades. On Together Through Life, he enlisted two incredible players from two classic American rock bands: Mike Campbell from Tom Petty and The Heartbreakers, and David Hidalgo from Los Lobos. On paper, this should have been one of his great guitar records. But Together Through Life is not that, almost perversely so. Instead, he keeps Campbell mostly in the background, and has Hidalgo add prominent accordion to several tracks. (“Soloing is not a big part of my records anyway,” he shrugged to Bill Flanagan upon the album’s release.)
In fact, the accordion informs the character of Together Through Life as much as Scarlet Rivera’s violin distinguishes Desire, though the effect isn’t as striking. (Speaking of Desire, “If You Ever Go To Houston” recalls that album’s cowboy-poet tales: “If you see her sister Lucy / Say I’m sorry I’m not there / Tell her other sister Nancy / To pray the sinner’s prayer.”) This record in general is more low-key than the three albums that preceded it, each of which came with strong narratives, whether it was Bob’s mortality (Time Out Of Mind), the end of the 20th century (Love & Theft), or the bleakness of contemporary life (Modern Times.) This album, in comparison, is composed mostly of love songs, with the occasional lament about your wife can really get on your back sometimes.
31. Dylan (1973)
The default “worst” Bob Dylan album. At least it used to be. It’s long been assumed to be an act of revenge against Dylan by Columbia Records for briefly leaving the label for David Geffen’s Asylum in the early ’70s. Dylan compiles 10 outtakes recorded during the period when he made 1970’s Self Portrait, another default “worst” Dylan album for many years. Bob apparently didn’t want it released, and he definitely didn’t sign off on the garish cover, a psychedelic head shop confection that seems designed with the expressed purpose of annoying a person as instinctually anti-hippie as Dylan.
But Dylan doesn’t really read that way now. For one thing, Bob Dylan himself has knowingly signed off on album covers that are much worse. (We will be revisiting some of those covers soon!) But the reputation of the Self Portrait era has been dramatically rehabilitated in recent years, thanks to the tremendous 10th volume of The Bootleg Series, Another Self Portrait, which recontextualized Dylan’s ’69-’71 years as a Basement Tapes-like era of playful exploration. You hear him dig deep into country music, traditional folk ballads, early rock ‘n’ roll, and contemporary singer-songwriters with an unselfconscious fandom and decidedly non-superstar humility. And that carries over to Dylan, which sounds less like spiteful corporate sabotage than another opportunity to hear a relaxed Bob Dylan explore a broad range of songs — courtesy of Joni Mitchell, Jerry Jeff Walker, Hank Snow, and others — with some of the best studio musicians ever.
What ultimately helps an album like Dylan is hearing it as part of his overall body of work, rather than his latest eagerly anticipated “statement.” This is the luxury of listening to this music several decades after the fact — his loose, low-stakes records have finally found their niche as some of his most guileless and approachable music.
30. Pat Garrett And Billy The Kid (1973)
The shock of listening to Dylan’s run from Nashville Skyline to the soundtrack for Pat Garrett And Billy The Kid — the doomed western directed by Sam Peckinpah in which Dylan appears as a mostly silent enigma named Alias — is how the poet laureate of rock gradually de-emphasized lyrics to the point of finally making a largely instrumental record. At the time people interpreted this as Bob having nothing to say. But now it seems like a creative masterstroke. He had already demonstrated his ability to cram 75 words into a single sentence. Now he wanted to show off some of his other tools.
For as celebrated as he is for his lyrics, Dylan’s melodic sense is still a little under-appreciated. Pat Garrett And Billy The Kid was an opportunity to be almost solely melodic, with the focus put on the sound of his jingle-jangly guitar and some understated accents from a supporting cast that included old friends like Roger McGuinn, Bruce Langhorne, and Jim Keltner.
This album of course is best known for “Knockin’ On Heaven’s Door,” a spooky, high-lonesome whistle past the graveyard that gave Bob an FM radio hit at a time when he had just about completely fallen off the pop-culture map. (It was later covered by Guns N’ Roses, at a different time when Bob had just about completely fallen off the pop-culture map.) But I find myself more mesmerized by the gorgeous, exhausted instrumental sections. Pat Garrett And Billy The Kid has an “end of an era” vibe that reminds me of David Crosby’s If I Could Only Remember My Name, in which another lion of the 1960s tiredly beats his guitar in the twinkling pre-dawn moments before a new day is about to begin.
29. Tempest (2012)
Pat Garrett And Billy The Kid was Dylan’s Peckinpah soundtrack, but Tempest is his Peckinpah film. Lots of blood and guts on this record, and I’m not just referring to the insane 13-minute song about the sinking of the Titanic. Much of the material here dwells on murderous tales that feel ripped from the Old Testament or a Cormac McCarthy novel. Like my favorite track “Tin Angel,” in which Dylan relates, in an even-gnarlier-than-usual croak, a gripping story about marriage, adultery, and revenge that unfolds against a slight bass pulse and a relentless banjo strum.
And then there are the songs where Bob also injects sex into the salacious mix, like “Narrow Way”: “I’m still hurtin’ from an arrow / That pierced my chest / I’m gonna have to take my head / And bury it between her breasts.”
While promoting the album, Dylan admitted that Tempest was “not the album I wanted to make,” indicating that he originally had “something more religious” in mind. More New Testament than Old, perhaps. But I now hear Tempest as a dry run for Rough And Rowdy Ways, an album it resembles in many respects, especially in terms of their gleeful obscenity and propensity for long, tragic story songs.
28. Good As I Been To You (1992)
He thought he was done making records after Under The Red Sky. But Bob Dylan is, if nothing else, a man who changes his mind. First, he entered a Chicago recording studio in the summer of 1992 and put down a bunch of covers with a band. Then he scrapped that album and made a record of folk and blues songs in his garage in Malibu. The garage record is what stuck.
Good As I Been To You feels like a lost album in Dylan’s discography, because it came out at a time when his stock was probably at its lowest. The month before it came out, Dylan was feted at Madison Square Garden with a 30th-anniversary concert marking the release of his self-titled debut album. But the purpose of that all-star show was to pay homage to Dylan’s songwriting, and here he was playing stripped-down versions of ancient tunes like “Jim Jones,” “Diamond Joe,” and “Froggie Went A-Courtin’.” This was also when grunge was at its height, and boomer rockers like Neil Young and Tom Petty were cranking the amps to fit in better with young bands. And here was Bob banging away on an acoustic guitar in his garage. He was on an island. But that’s not such a bad place to be when you’re a loner.
If this album — and it’s companion World Gone Wrong — didn’t make a whole lot of sense when they came out, they now seem to fit with the pattern of retrenchments that have taken place throughout his career, whether it’s the laidback county and folk of John Wesley Harding and Nashville Skyline in the face of ’60s psychedelia, or even his American standards albums of the ’10s. At some point, Bob feels a need to “bring it all back home” to music that is deliberately out-of-step with the larger world. And then he waits for the rest of us to catch up.
27. Saved (1980)
One night in the fall of 1978, Bob Dylan was alone in a hotel room in Tucson. He was on the final leg of a year-long world tour that was being critically savaged in the States. His latest album, Street-Legal, had also been dismissed in the press, as had his debut directorial effort, the four-hour Renaldo And Clara. His personal fortunes were somehow worse than the state of his career — he had recently divorced his wife, Sara, and he was nearing his 40th birthday, which in the late ’70s seemed like a death knell for a rock star.
In the face of so many crises, Dylan was understandably despondent. He felt ill during the previous night’s show in San Diego, and now felt even worse. He later recalled saying aloud, “I need something tonight.” He then reached into his pocket and found that something. It was a crucifix, which he had pocketed after it was tossed at him on stage during the San Diego concert.
“Jesus put his hand on me,” he claimed in a 1980 interview. “It was a physical thing. I felt it.”
With that, Dylan commenced the most controversial period of his career. What’s kind of amazing about Dylan’s so-called “born again phase” is that at first people actually seemed to actually like it. “Gotta Serve Somebody,” the single from his first religious LP, Slow Train Coming, was a Top 40 hit and won a Grammy. So, you can understand why Bob felt emboldened to put God’s big hand on the cover of his next album, Saved.
Man, what a cover! Bob’s best “worst” without question. Though the literal heavy-handedness of that image tends to obscure the music on Saved, which to my ears picks up the gospel-rock thread of Slow Train Coming with only a slight drop-off. Yes, the lyrics offer a litany of unequivocal polemics — in “Are You Ready” he asks, “Have you decided whether you want to be / In Heaven or in Hell?” — but Bob at this time was singing very well and writing stirring music. “Covenant Woman,” “Solid Rock,” “Pressing On” — these are all good, beautiful songs.
For years, people wanted Bob Dylan to spell out exactly what he thought, without the guise of poetry or metaphor. This is the central irony of Saved: The message couldn’t be more clear. It was the one time he embraced being a spokesperson who stumped for a specific cultural position, and the public was horrified!
26. Empire Burlesque (1985)
It’s inevitable that Bob Dylan’s path eventually crossed with film director Paul Schrader. Both of them were born in the 1940s and hail from the upper Midwest. They’re both fascinated by spirituality, morality, and how corruption poisons the soul. They both have written about famous boxers. They both seem like equally unchill dudes.
But who could have predicted that the Dylan/Schrader union would result in a music video as wondrously strange and just plain wrong (but in the absolute “right” way) as “Tight Connection To My Heart”? A quick plot synopsis for those who haven’t seen it: Bob is in a hotel room — not in Tucson, I think it might be Tokyo. A woman confronts him. We see her zoom in on a telephone number — 362-1795 — written on hotel stationery placed on Bob’s bedside table. Bob says his hands are sweaty. Then he’s arrested. The charges against him are unclear. And then we see, in a flashback, Bob weirdly caress the woman’s face. Is extreme awkwardness a crime?
After that, Bob is apparently on parole. He’s wandering the streets. He ambles into a bar and sees himself in a black leather suit playing guitar in a band. But wait, Bob is actually still under arrest and now he’s being interrogated. Are there three different Bobs? This storytelling device is reminiscent of Schrader’s masterful film Mishima: A Life In Four Chapters, which came out four months after Empire Burlesque.
Where was I? Oh yeah, Bob then mimes a guitar solo like he’s never actually played guitar before.
I could go on, but I fear I’m making this muddled but oddly lovable album even more confusing. Empire Burlesque is definitely one of those Dylan albums that for a long time I thought I hated, and then I talked myself into liking it, and now I actually like it. It’s the zany sequel to Infidels, with extremely ’80s production blown up and exaggerated to the point of endearing ridiculousness. Do you recoil at the thought of Bob turning himself into The Hooters on “When The Night Comes Falling Out Of The Sky”? I can’t blame you. But I do feel sorry for you.
25. World Gone Wrong (1993)
Bob’s second “Malibu garage” record. It’s ranked higher than Good As I Been To You because it’s darker, rawer, bluesier, more lo-fi, and just hits harder in the gut. It also has “Blood In My Eyes,” an old song by the Mississippi Shieks, “a little known de facto group whom in their former glory must’ve been something to behold,” as Bob relates in the liner notes.
Did I mention that Bob wrote the liner notes to World Gone Wrong? It’s a special treat reserved for those willing to pony up for a physical copy. Unlike the surrealist style he applied to the notes for his ’60s albums, Bob’s voice inside World Gone Wrong resembles the knowing and witty narrator of his 2004 memoir, Chronicles Vol. 1, and his aughts-era radio show, Theme Time Radio Hour. He’s wise and wry, and in on his own joke.
The best part is when he tries to set the record straight about the Never Ending Tour: “There was a Never Ending Tour but it ended in ’91 with the departure of guitarist G.E. Smith. That one’s long gone but there have been many others since then,” he writes. And then he makes up some great fake tour names: “The Money Never Runs Out Tour (fall of ’91) Southern Sympathizer Tour (early ’92) Why Do You Look At Me So Strangely Tour (European ’92) The One Sad Cry of Pity Tour (Australia & West Coast America ’92) Principles Of Action Tour (Mexico — South American ’92) Outburst Of Consciousness Tour (’92) Don’t Let Your Deal Go Down Tour (’93) and others too many to mention each with their own character and design.”
Finally, he adds, “To know which was which consult the playlists.” Maybe Bob should be the one writing a pithy ranking of Bob Dylan albums!
24. Bob Dylan (1962)
Here’s a thought experiment I like to play with the first Dylan record: Imagine a baby-faced kid from Minnesota who moves to New York, scores a record deal after about a year, and then makes an album composed almost entirely of old traditional material about death in the year 2021. How would that be received?
If Bob Dylan showed up today, would he seem like a poseur? A hipster? An extremely pretentious young man who might also be a pathological liar? I recognize that this is not a perfect analogy for our current moment. That 20-year-old kid in 2021 would probably make a post-punk album inspired by The Fall and sing songs about social anxiety and the vagaries of post-Trump America. I’m just trying to imagine how audacious this record must have seemed at the time, and what it would have felt like to hear that rough and rowdy voice come out of the kid on that album cover. Dylan looks like he’s 13 years old and about to deliver your morning newspaper, not the opening salvo in the greatest career in modern popular music.
I tend to think of Bob Dylan as the start of an amazing career more than an amazing record itself. He hadn’t really found himself yet. The songs he played on this album weren’t necessarily staples of his club shows at the time, and he didn’t perform most of the tunes all that much after 1963. And then there’s The Freewheelin’ Bob Dylan, a markedly better album loaded with future classics that came out the following year. But I love Bob Dylan anyway because the titular star had to have so much damn guts to even attempt an album like this.
23. Self Portrait (1970)
If you’re somehow not a Bob Dylan fan, and you’ve somehow gotten this far into the list, I suspect you’re most annoyed by the following: It seems like I have spent a lot of time justifying my love of albums that might, in fact, not actually be good.
I don’t think I have been doing this, because I think all of these albums are good, though admittedly in unconventional ways in some cases. Nevertheless, I understand someone who is not a Dylan fan thinking this. It’s true that the man has made a lot of flawed records. (He’s also made a lot of flawless records, but we haven’t gotten to that part of the list yet.) But if you invest a lot of time in listening to an artist, and thinking about an artist, and even writing about an artist, you will see the flaws in their art in the way you see flaws in a friend or family member, as essential quirks that make you love those people even more.
But I can see the limitations of this point of view, and one of those limitations is Self Portrait. Here’s a record that Dylan himself has said that he made bad on purpose, because he was sick of so many lunatic hippies showing up to his family pad in Woodstock and wanting to rap about organic farming. He wanted people to stop thinking of him as a spokesman of generation, so he made a record in which the opening track is about how when all the tired horses are in the sun, you really can’t get any riding done. Try to make that seem profound.
I guess the thinking was that Dylan fans would hear Self Portrait and immediately start bugging Paul Simon instead. So he emptied his kitchen sink: There’s a Gordon Lightfoot song, a weird performance of “Like A Rolling Stone” from the Isle of Wight, an incredible performance of “The Mighty Quinn (Quinn The Eskimo)” from the Isle of Wight, two different tunes named “Little Sadie,” and lots of AM country gold.
Music critics predictably hated it. (Greil Marcus’ dismissal is one of the all-time great rock-critic disses: “I once said I’d buy an album of Dylan breathing heavily. I still would. But not an album of Dylan breathing softly.”) But Dylan fans are so insane that they came to appreciate Self Portrait as a deconstruction of the “idea” of a Dylan album, a work of anti-profundity that was actually a profound act of self-criticism. Truth be told, I actually do appreciate the album on that level. But mostly — as I said about the similarly maligned Dylan — I just think a lot of this music is actually pretty beautiful, and I like that Dylan has so many albums that there’s space for a pisstake cover of “The Boxer” that allowed Bob himself the privilege of bugging Paul Simon.
22. Modern Times (2006)
Around the time of the “Malibu garage” records, something strange happened to Bob Dylan. He stopped seeming like a present-tense figure. I’m not saying he was irrelevant to modern music; on the contrary, this period coincides with Bob Dylan returning to mainstream esteem. I mean that in his songs and in his persona, he seemed like a guy whose body was in our time but whose mind and aura were teleported from the mid-20th century. It’s hard to imagine him shopping at Costco or watching The Masked Singer or listening to dirtbag left political podcasts. Bob Dylan plays mid-20th century music, and he dresses like an entertainer from the mid-20th century. He’s like John Wayne in The Searchers, a man out of time.
Modern Times for the most part fits with this archaic image that Dylan has embraced for almost 30 years. Incredibly, it topped the charts anyway in 2006, one week after the self-titled debut by Danity Kane and one week before Beyoncé’s B’Day. It’s like everyone decided to watch Bonanza reruns for a week instead of American Idol.
Of course, Bob Dylan does live in our world. It’s just a little jarring when he reminds us of that fact. Which is why the lyric everyone remembers from Modern Times is this part from the album-opening “Thunder On The Mountain”:
I was thinkin’ ’bout Alicia Keys, couldn’t keep from crying
But she was born in Hell’s Kitchen, I was living down the line
I’m wondering where in the world Alicia Keys could be
I been looking for her even clear through Tennessee
21. Shot Of Love (1981)
In reality, around the time that Alicia Keys was born, Bob Dylan was getting ready to make his 21st album, Shot Of Love. This one would go down as his “half-Christian” record, with some songs explicitly referencing Jesus (including “Property Of Jesus, in which Bob once again pledges fidelity to the Lord, though he seems to be really singing about himself and the reception of his religious records) and other songs that brought Bob back to the secular world (like “The Groom’s Still Waiting At The Altar,” a B-side so good it was added to the album when it was reissued on CD).
Bob always talks about how underrated Shot Of Love is, and I agree with him. The main attribute of this record is how ragged and spontaneous it is. Producer Chuck Plotkin, who normally worked in a much more methodical way with Bruce Springsteen on some of his most famous albums of the ’70s and ’80s, had to quickly grab a microphone and hold it in front of Dylan’s face after he suddenly started playing “Every Grain Of Sand” for the first time. And then there’s “Lenny Bruce,” Dylan’s homage to the late comic legend, who in his estimation was an “outlaw” who deserved praise even though he “never did get any Golden Globe award.” It’s a strange and kind of mawkish ballad, but Dylan (as he did throughout his religious period) sings it with great feeling. (I also have a soft spot for “Lenny Bruce” because I saw Bob play it on his 2019 tour, which I hope is not his last.)
Let’s all take a moment, stretch our legs, and enjoy this weird but charming Bob Dylan cameo from season three of Pawn Stars.
20. Another Side Of Bob Dylan (1964)
Like the man himself once said, things should start to get interesting right about now.
From here on out, as we near the top of Bob mountain, the rankings become more treacherous and harder to navigate. Aside from a handful of albums at the very top, many of these records could be placed elsewhere on my list if I happened to doing this on a different day.
But I happen to be writing this on this day, which is how an album that has “My Back Pages,” “Chimes Of Freedom,” “It Ain’t Me Babe,” and “I Don’t Believe You” ends up at No. 20. This record is obviously historically significant — it was Bob moving beyond the overt polemics of The Times They Are A-Changin’ and moving into the personal songwriting that distinguishes his mid-’60s glory years. Another Side Of Bob Dylan also has a cool backstory, including a trip to Europe in which Dylan hung out with Nico, who I’m sure looked impossibly glamorous while Bob put the finishing touches on most of the songs he would subsequently record in a single night — June 9, 1964 — with producer Tom Wilson while downing several bottles of wine.
I love all of that stuff. What I don’t love is “Ballad In Plain D,” the most aggregiously cruel song in the Dylan catalogue, which describes the collapse of his relationship with Suze Rotolo and his unsparing feelings toward her sister and mother. “Ballad In Plain D” is not only mean-spirited and self-pitying — “For her parasite sister, I had no respect,” yikes! — but it’s also really, really long. Dylan later called himself a “schmuck” for writing it. If only he could have been born 40 years later and had access to Tumblr in his early 20s, he could have vented his spleen in a less permanent venue.
19. Planet Waves (1974)
Tour 74 — the massive 40-concert arena campaign that Bob Dylan performed with The Band in January and February of 1974 — was the most hyped rock event of the era. David Geffen called “the biggest thing of its kind in the history of show business.” They were supposedly 20 requests for each ticket sold. Newsweek put Bob on the cover (back when that was a big deal) under the headline, “Dylan’s Back!” By the summer, a double live album, Before The Flood, was released and eventually went platinum.
That tour was so big that it overshadowed the studio album that Bob recorded with The Band and released two weeks into the tour. Planet Waves didn’t factor much into the setlists for Tour 74, which was largely a greatest hits affair and not really a “support” campaign for Dylan’s latest work. Waves was followed up by Blood On The Tracks, the defining masterpiece of his 30s, and then Desire, which coincided with another iconic concert tour, Rolling Thunder. A few years after that, you have the Christian era, which is a whole other saga. All the while, Planet Waves seems sort of forgotten.
But what a record! In contrast with the bombastic Before The Food, Planet Waves is a relatively unassuming affair. On stage, Dylan and The Band reverted to the aggressive barnstorming of their original partnership back in 1966. But on record, the playing is far homier and more relaxed, like if The Basement Tapes had been made in an L.A. recording studio rather than a pink house in upstate New York. This vibe plays down the romantic discord that runs through several songs, which would achieve full fruition on the forthcoming Tracks.
18. New Morning (1970)
Another overlooked classic, at least before The Dude made it his favorite Bob Dylan record. At the time, it was perceived as a makeup record for the poorly reviewed Self Portrait, which came out only four months earlier. (Bob Pollard had nothing on Bob Dylan in 1970.) But now those two records now feel like complementary works, with New Morning acting as the slightly slicker version of Self Portrait‘s good-natured celebration of normie domesticity.
By 1970, Bob was through with Desolation Row. Like he says in “Winterlude,” “Tonight there will be no quarrelin’ / Ev’rything is gonna be all right.” The love songs are what stand out in my mind — “The Man In Me,” “One More Weekend,” and “If Not For You,” which is my wedding song, so I’m required at the very least to put New Morning in the top 20. But this album is weirder than you remember. “If Dogs Run Free” is a callback to the playful perversity of Self Portrait, which is one of the aspects of Dylan’s work at this time that I dig so much. The guy was never afraid of being silly, and he’s more self-aware about this than he often gets credit for. He let the dogs out 30 years before The Baha Men.
And then there’s “Time Passes Slowly,” in which this icon of the counterculture sings moonily about romanticized small town life “up here in the mountains” where people “sit beside bridges and walk beside fountains.” Given that America was being ripped apart in 1970, you could accuse Dylan of sticking his head in the sand by making such an idyllic record. But 51 years later I’m just happy to stare into those lovely fountains.
17. Rough And Rowdy Ways (2020)
A landmark for many reasons. It might be the best album ever released by a 79-year-old. It might also have the worst cover of any Dylan album, a true achievement considering the stiff competition. (Shoutout to Shot Of Love and its horrific pop-art cover, which Andy Warhol should’ve sued over.) It is certainly the first Dylan album to include the word “cock.”
But for me the conversation about Rough And Rowdy Ways begins and ends with the final track, the nearly 17-minute “Murder Most Foul.” Of all the hundreds of songs that Dylan has written, “Murder Most Foul” stands alone as a singular achievement without precedence. A jazzy dreamscape with no discernible melody and scores of tangents springing from a central narrative about the JFK assassination, “Murder Most Foul” is ASMR for the apocalypse, a hypnotic deconstruction of modern American history that is both terrifying and hilarious, with Dylan riffing over three pianos played by Fiona Apple, Benmont Tench, and longtime Dylan sideman Alan Pasqua.
“Murder Most Foul” is a remarkable song, but it’s an even more remarkable gesture of Dylan’s willingness to still experiment, confound, innovate, and exist on his own totally weird wavelength. The same can be said of the rest of the album, which found Dylan, incredibly, once again reenergizing creatively on the eve of entering his 80s.
16. Slow Train Coming (1979)
With apologies to Jesus Freak, this is the greatest Christian rock album ever made. DC Talk didn’t have the benefit of working with producers Jerry Wexler and Barry Beckett and half of Dire Straits playing behind him. Yes, some of the evangelical lyrics are a little judge-y — “Ya either got faith or ya got unbelief and there ain’t neutral ground” is the most wince-inducing — but Bob’s musical acumen was better than ever when he became his own kind of Jesus freak.
Slow Train Coming might have God on the mind, but the devil is in the grooves. It’s absolutely killer soft-rock gospel. I love the part near the end of “Gotta Serve Somebody” when Bob breaks down all the things you can call him: Terry, Timmy, Bobby, Zimmy, R.J., and Ray. He doesn’t mention his actual middle name, Allen, but on side two he does perform a reggae song called “Man Gave Names To All The Animals” so maybe he was a little distracted. And then the album ends with “When He Returns,” in which Dylan delivers a vocal so impassioned that even atheists might be moved to temporarily suspend their disbelief.
15. Nashville Skyline (1969)
Bob Dylan has never given a straight answer about that voice he uses on Nashville Skyline. In 1969, he told Jann Wenner his voice changed after he briefly quit smoking. “I tell you, you stop smoking those cigarettes . . . and you’ll be able to sing like Caruso.” Sure Bob. Only you don’t sound like Caruso, you sound like a conniving teenager lowering his voice in order to call in himself sick at school. On paper, it’s so goofy and shouldn’t work at all. But this is Bob Dylan, an avatar of American self-invention, so the contrivance works brilliantly, even when Bob dares to put himself next to the barrel-chested baritone voice of modern music, Johnny Cash.
Nashville Skyline is a little flimsy in places. It’s only 27 minutes, and that’s even with obvious filler like the instrumental “Nashville Skyline Rag” and the should’ve-been-an-instrumental “Peggy Day,” in which he rhymes “day” with “away,” “say,” and “gray.” But as a vibe? Nashville Skyline is undefeated. There’s a reason this album comes before his domestic album New Morning. You have to make kids before you raise them. Put this album on at sunset, open a bottle of wine, steer your romantic partner toward a big brass bed and … do I need to draw you a road map?
14. The Freewheelin’ Bob Dylan (1963)
Another thought experiment: Let’s say Bob Dylan died after the release of his second album. How would that affect his legacy? For starters, this list would only be two albums long. The Freewheelin’ Bob Dylan would be the top ranked Dylan record, and the self-titled Bob Dylan LP would be the lowest ranked. All this other music we’ve been obsessing over wouldn’t exist. Which would be tragic, but consider the body of work he would have already left behind in 1963: “Blowin’ In The Wind,” “Girl From The North Country,” “Masters Of War,” “A Hard Rain’s A-Gonna Fall,” “Don’t Think Twice, It’s All Right,” plus “Song For Woody” and “Baby Let Me Follow You Down” from the first record. Just based on that small but momentous output, he’s Ian Curtis or Kurt Cobain. An undeniable “tragic” icon.
I used to really resent Freewheelin’ when I was in my early 20s, but I couldn’t believe that a guy so young was capable of writing those songs. It makes you feel worthless as a 21-year-old to hear “Masters Of War” or “Don’t Think Twice, It’s All Right” and realize you aren’t even capable of doing your own laundry, much less creating art already seems ancient and true in ways even Dylan himself probably couldn’t fathom at the time. How many early 20somethings have early Bob Dylan made feel insecure about their accomplishments? The only consolation comes from the man himself: He was so much older then, he’s younger than that now.
13. Infidels (1983)
The first “best Dylan album since Blood On The Tracks” Dylan album. After the three gospel records, many people were relieved to see him now writing secular songs. But Infidels doesn’t leave moralizing (or eccentricity) behind. Like a lot of Christian rockers, Bob realized he could win over mainstream audiences by just leaving out the words “God,” “Jesus” and “the devil.” So, he wrote “Jokerman,” his great reggae anthem, in which he’s probably singing about the devil or at least a man who just wants to watch the world burn. The most reactionary lyric from Infidels is from “Sweetheart Like You,” where Bob says, “You know a woman like you should be at home / That’s where you belong.” But I’m most confused/delighted by “License To Kill,” in which Bob expresses his misgivings about the space program. (Thankfully, he changed course on Shadows In The Night, singing, “The moon is there for us to share.”)
As much as I adore Infidels as it is, it might have been a top 10 album for me if it had included two songs recorded during the album’s sessions but inexplicably left off the record: “Blind Wille McTell” and “Foot Of Pride.” Bob did this a lot on his ’80s albums, as his ability to discern his best material seemed to have temporarily abandoned him. (Along with his self-consciousness about wearing leather vests with no shirt underneath.) But Infidels is the best/worst example of this phenomenon. A great album that could have been an all-time masterpiece.
12. Oh Mercy (1989)
The first of two albums in the “Daniel Lanois” subgenre of Dylan records. Dylan himself seems ambivalent about his work with the Canadian super-producer. In his book Chronicles, he writes of Oh Mercy, “The kind of music Danny and I were making was archaic. I didn’t tell Danny that, but that’s honestly how I felt.” But I suspect that his main problem is that Lanois didn’t work in the same way Dylan did, which usually involved going in with a band, playing live, and recording take after take until he serendipitously landed on the sound in his head. Lanois instead preferred to start with Bob, get a strong vocal, and then place overdubs around it. It’s the difference between being an artist and being an architect.
Now, as you can tell by the ranking, I love the Lanois albums. But they do feel like collaborations between Bob and his producer in a way none of his other albums do. Dylan’s songs on Oh Mercy are wonderful — “Most Of The Time,” “Shooting Star,” “Man In The Long Black Coat,” “Ring Them Bells” — but the wide open spaces in the recordings of those songs, and the rich bass tones and guitar sighs and insects and smoke that fill them, belong to Lanois. I’m sure hearing so much of that other guy in his music annoyed Dylan on some level. But he could also see that it worked, and that it also provided a counter-example that inspired him when he started producing his own albums in a much more naturalistic way starting in the early 21st century.
11. Love And Theft (2001)
His first record after winning the Album Of The Year Grammy for Time Out Of Mind, a great ’90s comeback story on par with John Travolta becoming a star again in Pulp Fiction. Bob responded by making his Face/Off, a much wilder and funnier record. Gone were the swampy sonics and ponderous “mortality” sermons. This was Bob plugging in with his crack tour band — all hail Larry Campbell and Charlie Sexton, the best Dylan guitarists not named Robbie Robertson — and being a street-savvy wiseass again.
What a thrill! Bob was back to being cocky like he hadn’t been since the mid-’60s. In “Summer Days,” he straightens out the doubters who think he’s a worn-out star. “She says, You can’t repeat the past,’ I say, ‘You can’t? / What do you mean, you can’t, of course you can!'” This was prime “side one of Bringing It All Back Home“-level swagger.
And that attitude carried over to his interviews about the record. Years later, Mikal Gilmore pressed him about accusations that he lifted lines from Japanese writer Junichi Saga for the song “Floater.” Dylan scoffed, “Wussies and pussies complain about that stuff. It’s an old thing – it’s part of the tradition. It goes way back. These are the same people that tried to pin the name Judas on me. Judas, the most hated name in human history!”
He was still mad about “Judas!” The piss and vinegar of this man’s golden years is a sight to behold. As much as I treasure Love And Theft, I would trade that album for a tape of Bob Dylan saying “wussies and pussies.”
10. Street-Legal (1978)
The “lyrically dense” Dylan album. Many Dylan albums are lyrically dense, but this one is lyrically dense even by Dylan standards. I’ve played this album hundreds of times and I think I understand about .01 percent of it. I get what “New Pony” is about — Bob is into sex. And I think I comprehend “Where Are You Tonight? (Journey Through Dark Heat)” — Bob is staring in the mirror in order to understand himself and his dark and brooding Dylanesque hotness. But “Changing Of The Guards” is still a mystery to me. Is this song a metaphor for Bob’s career? Is Bob literally a time traveler from the 8th century? Are both interpretations simultaneously true?
A few years ago, I became obsessed with “solving” the third track on Street-Legal, “No Time To Think.” It’s an incredible lyrical construction, in which internal rhymes are tucked inside of external rhymes and then stacked on top of each other into a fascinating, befuddling puzzle.
Warlords of sorrow and queens of tomorrow
Will offer their heads for a prayer.
You can’t find no salvation, you have no expectations
Anytime, anyplace, anywhere.
Finally, after staring at my copy of Lyrics 1962-1985 for about an hour, I concluded that Bob just really likes to make things rhyme. And he rhymes his ass off here. And he also rocks his ass off. Bob was understandably irked when it was pointed out that Street-Legal sounds a bit like The E Street Band. But this sax-heavy, arena-rock sound — also immortalized on the radical and totally brilliant live LP Bob Dylan At Budokan, which is just as confrontational to fixed ideas of how Dylan is as his 1965-66 “electric” tour — suited him surprisingly well. On Street-Legal, the lyrics are Dylan at his most inscrutable and the music is Dylan at his most accessible. A tuneful, blissful confusion.
9. The Times They Are A-Changin’ (1964)
The peak of his “finger-pointing” period. But what I love about it is the storytelling. In this incredible mid-’80s BBC interview — Bob is wearing heavy eye shadow and looks like he hasn’t showered since 1977 — he dismisses the idea that he writes stories, because stories have a beginning, middle, and end. And many Dylan songs are only beginnings and endings, or they might start in the middle and then go back to the beginning or forward to the end. But they aren’t necessarily coherent narratives. The Times They Are A-Changin’ is an exception to the rule. These are songs you can see as much as hear.
The power of “The Lonesome Death Of Hattie Carroll” is that it’s more like a biopic than a polemic — it sketches characters and events in economic yet highly visual language, so that the moral outrage ultimately derives from watching William Zanzinger get away with murder on the screen in your head. And then there’s “The Ballad Of Hollis Brown,” a brutal tale of murder on the prairie in which Bob Dylan makes his own version of Nebraska 18 years before Bruce Springsteen. But whereas Springsteen made a career out of being rock’s consummate storyteller, Bob dabbled in this style of linear narrative, mastered it, and then moved on. He would soon be emulating Rimbaud and Allen Ginsberg, but on this record he was more like Sidney Lumet.
8. Desire (1976)
Bob’s other great “storytelling” record. You have “Hurricane,” of course, in which Bob proves that all true crime podcasts need only be eight minutes long so long as your co-host is Emmylou Harris. You have “Isis,” a tale about a rocky marriage told against the backdrop of an adventure story directed by Steven Spielberg. You have “Sara,” a song about Bob’s own rocky marriage in which a deserted beach except for some kelp functions as an emotionally crushing signifier of a loveless union.
True, you also have “Joey,” Desire‘s most notorious clunker, which the tracklist says is 11:05 but I’m pretty sure is really about 200 times longer than that. Lester Bangs explained what’s problematic about “Joey” better than I ever could, but what bugs me most is that Bob chose to put that song on instead of the sublime “Abandoned Love,” which would have shot Desire into the highest stratosphere of Dylan albums. But I’m a forgiving person when it comes to an album that also includes “One More Cup Of Coffee,” “Oh Sister,” and “Romance In Durango,” which like “Isis” transformed into a fire-breathing dragon on the Rolling Thunder tour.
7. Bringing It All Back Home (1965)
Overall, this is the seventh ranked album on my list. But side two of Bringing It All Back Home is the greatest side of any Dylan album. You start with “Mr. Tambourine Man,” which on many days is my favorite Bob Dylan song of all time. You have “Gates Of Eden,” in which Bob wrests superhuman feats of prose out of his cranium such as “the motorcycle black Madonna / Two-wheeled gypsy queen.” You have “It’s Alright, Ma (I’m Only Bleeding),” the single most quotable song in the Dylan canon. (I’ll call “money doesn’t talk, it swears” as the best line, but I’m fine if you go with “but even the president of the United States sometimes must have to stand naked.”) And finally there’s “It’s All Over Now, Baby Blue,” the song that literally murdered Donovan in Don’t Look Back.
Am I wrong to think that side one seems a little flimsy compared to that? It’s supposedly the forward-thinking side, with Bob dabbling with electric instrumentation. Obviously, there are some serious classics here: “Subterranean Homesick Blues,” “She Belongs To Me,” “Maggie’s Farm,” and “Love Minus Zero (No Limit)” are all beauties. But compared with what’s about to come, Bob’s attempts to rock on Bringing It All Back Home sound like skiffle. When I reach for this record, I can’t help but fixate on the side in which Bob only exploded the possibilities for rock songwriting forever.
6. Time Out Of Mind (1997)
“Well . . . the Time Out of Mind record, that was the beginning of me making records for an audience that I was playing to night after night,” Bob said in 2012. “They were different people from different walks of life, different environments and ages. There was no reason for these new people to hear songs I’d written 30 years earlier for different purposes. If I was going to continue on, what I needed were new songs, and I had to write them, not necessarily to make records, but to play for the public.”
I think a big reason why this album means so much to me is that I was part of the audience that Bob is referring to here. Time Out Of Mind was the first Dylan masterpiece to come out when I was paying attention, as a guy in his late teens who was just starting to wrap my head around his catalogue. Time Out Of Mind indicated that Dylan was actually worth still paying attention to, and that he might even have something to say to a younger generation. Which might be a strange thing to say about an album of dusty blues, lurching torch songs, and one meandering 16-minute song set in a mystical diner.
But the very fact that Bob had given up on trying to keep up with the kids made him appealing to kids like me. Music critics are paid to find cultural meaning in pop music, but the fact is that so much pop is ephemeral and embossed with an alarmingly brief expiration date. You spend too much time listening to it and you find that the world also seems ephemeral and constantly on the verge of extinction.
But Bob Dylan’s music doesn’t feel that way. Time Out Of Mind is known as Bob’s mortality record, a distinction the man himself hated. (“I didn’t see any one critic say: ‘It deals with my mortality’ — you know, his own. As if he’s immune in some kind of way,” he once scoffed.) But Time Out Of Mind resonated then and it resonates now because that record has a sense of immortality. Like so many Dylan records, it reminds you that human beings have been around for a long time, and they’ve always cared about the same things: love, hate, fear, pleasure, God, the devil, and, yes, death. As dark as this album is, it’s also reassuring. People, in spite of everything, endure. That includes Bob, who has outlived his mortality album by 24 years and counting.
5. The Basement Tapes (1975)
Every now and then, an argument will bubble up about such-and-such-songwriter being better than Bob Dylan. The “such-and-such-songwriter” part is always different, but the “better than Dylan” part is always the same. Which seems like a self-negating premise: If Bob Dylan is always the standard by which other songwriters are measured, doesn’t that make the conversation moot?
It’s true that there are songwriters who are better than Bob Dylan in specific ways. Joni Mitchell was a better musician. Neil Young (maybe) put out better albums in the ’70s. Leonard Cohen might have been a more technically proficient poet. Prince looked better in assless chaps. But in terms of the overall picture — a man who has put out 39 albums in various styles over the course of nearly 60 years — Dylan is unmatched. You can beat him in a sprint. But he’s a champion marathon runner.
Consider this: One of his prolific years as a songwriter occurred when he was supposed to be nursing a damn broken neck. And then he didn’t bother to release any of those songs for another eight years (and many more of them for another 47 years). In the process, he accidentally invented two long-lasting rock tropes: the bootleg album, and the “let’s go to the country and make weird and mind-blowing American roots music” album.
For most artists, The Basement Tapes would be an entire career. For Bob Dylan, it’s a career chapter. That’s what separates him from all the people who are supposedly “better” than him: Breadth.
4. Highway 61 Revisited (1965)
Here’s where my rankings become impossible. How do you choose between the albums that are left? This is the first Dylan I ever loved, and I suspect it’s the one many other Dylan fans loved first. Bruce Springsteen once described hearing “Like A Rolling Stone” and it sounding like “the toughest voice I ever heard … a guy that had the guts to take on the whole world, and made me feel like I had ’em, too.” I felt exactly the same way the first time that Highway 61 Revisited clicked for me. I was an angry young man, and I connected with the anger that Dylan had as a young man. But more than that, I was awed by his courage. Here was a person who could sing “the sky’s not yellow, it’s chicken” with fearless conviction. It made sense because he demanded that it make sense.
That confidence was doubly inspiring when I heard the historic “Royal Albert Hall” show when it was still a bootleg. You could boo Bob Dylan, you could slow-clap over his songs, and you could even call him Judas. But you couldn’t defeat him. He was always ahead of you. From then on, he was my hero.
This past summer, I went for a drive at dusk with Highway 61 Revisited. My initial plan was to play “Like A Rolling Stone” and maybe “Tombstone Blues,” but of course I stuck around for the whole thing. At the end of the record, I suddenly got choked up during my favorite moment on the entire album, the first harmonica solo in “Desolation Row” where it sounds like Bob’s lungs could spontaneously combust at any moment. He blows so hard, and the harmonica screams louder than anything you’ve ever heard, and during those 52 seconds you feel as invincible as he must have felt when he laid it down at Columbia Studio A in New York City. I broke down because I thought about myself at 19 and how much I needed Bob Dylan to make me feel temporarily invincible. And I thought about how much I still need him in order to feel that way now.
3. John Wesley Harding (1967)
Before we talk about what Bob does here, let’s give it up for the other two guys who play most of the music on John Wesley Harding: bassist Charlie McCoy and drummer Kenny Buttrey. I don’t know how to describe what they do on this record. Bob is playing Old Testament folk songs, and McCoy and Buttrey are two shit-hot Nashville studio cats. But John Wesley Harding isn’t really folk, and it’s certainly not country. For one thing, McCoy and Buttrey groove like crazy; the rhythm section is at least as prominent as Dylan, whose jangly acoustic guitar defers to McCoy’s looping bass lines and Buttrey’s jittery syncopations. You could almost dance to John Wesley Harding, but just almost. Did Bob invent the Meat Puppets? John Wesley Harding is proto-cowpunk.
I’m probably only person who feels this way but: I’m a little disappointed that Bob plays “All Along The Watchtower” the way Jimi Hendrix did it on Electric Ladyland, rather than the way he did it on John Wesley Harding. My theory is that Bob secretly knows that he can’t do it the John Wesley Harding way without McCoy and Buttrey laying it down with him. He never sounded like he did on that record before, and he never would again. It’s an island onto itself in his catalogue. He didn’t even bother to use any of the Basement Tapes tracks for the album. This was its own thing. Dylan got it out of himself, and maybe he is still trying to understand it.
Can I rave for a minute about Bob’s harmonica playing? This is his pinnacle on the harp; he plays it on everything, and he plays it beautifully. At the end of “I Dreamed I Saw St. Augustine,” Bob sings about waking up from a nightmare and then bowing his head to cry. And then he actually weeps into his harmonica. It’s breathtaking. And there’s at least one moment like that on every track from this simple, mysterious, bottomless, strange, profound, and thoroughly ravishing record.
2. Blood On The Tracks (1975)
Let’s start with the title. What a title! Even before you put it on, Blood On The Tracks sounds like a monumental record. The title evokes a train accident. It also implies that Bob put his literal guts into the album tracks. Ultimately, it promises to be a heavy listen, and it is.
The first time I heard it, I had never been in a serious relationship. Blood On The Tracks therefore was a sneak preview of what being an adult is like. My appreciation of Bob’s pain was voyeuristic; I was actually jealous that I hadn’t had my own heart broken yet. I assumed that when my own romantic apocalypse came down, I would be as eloquent as Bob.
But that didn’t happen. When I finally was demolished by love, I could hardly speak at all. Blood On The Tracks spoke for me. Some of the songs became unbearable to play, like “You’re A Big Girl Now,” where Bob pleads, “I can change I swear.” The toughest listen was “If You See Her, Say Hello,” which includes scenes as brutal and honest as any Cassevetes film. You shouldn’t be allowed to operate heavy machinery and hear Bob Dylan sing, “I’ve never gotten used to it / I just learned to turn it off.”
But even when I was down in the romantic dumps I kept on listening. Eventually, when I was no longer demolished by love, I could see how much romance is also in this record. When I got married, I read the lyrics to “Shelter From The Storm,” save for the last few verses where everything goes to hell. I can’t think of a better description of my wife than this: “Try imagining a place where it’s always safe and warm.” Bob keeps himself aloof because at heart he’s the biggest softie in the world.
Sometimes I think this is my favorite Dylan record. But then I remember that “Up To Me” was left off and I have to say it’s my second favorite.
1. Blonde On Blonde (1966)
A scene I think about a lot is the part in No Direction Home where Joan Baez is sitting in her spectacular kitchen and trying to explain why Bob Dylan is so meaningful to a certain kind of person. A lot of people hear Bob Dylan and feel nothing, she concedes. But for the people who are affected, it goes deep.
For me, Bob goes deep. And this one goes the deepest. I could write a Wikipedia entry on how this album changed rock, reinvented the singer-songwriter genre, created “the 1960s” as a concept, and paved the way for excessive double albums in popular music for several decades. But all that really matters is that Blonde On Blonde goes deep.
The hurt in his voice in “Just Like A Woman” goes deep. The romance of “I Want You” goes deep. The way that “One Of Us Know (Sooner Or Later)” snaps like that into being goes deep. The wailing harmonica solo in “Absolutely Sweet Marie” goes deep. These lines from “Visions of Johanna” go deep:
Lights flicker from the opposite loft
In this room the heat pipes just cough
The country music station plays soft
But there’s nothing, really nothing to turn off
On many days “Visions Of Johanna” is my favorite Bob Dylan song of all time. I know I just said that about “Mr. Tambourine Man,” but I could say it about another 100 Bob Dylan songs, just as I could say that every album on this list is my favorite Bob Dylan album. No body of work means more to me. I’m so damn glad that this music, and the man who made it, exists. May you stay forever young, Bob.