The 10 Best More-Obscure Bob Dylan Albums

The 10 Best More-Obscure Bob Dylan Albums

When dealing with any individual possessing the sheer magnitude of Bob Dylan — a figure utterly massive in terms of talent, mythology and self-regard — it becomes difficult to speak to his “lesser” or “more obscure” works. All of his 35 studio albums, scores of live albums, best-of collections, and official and unofficial bootlegs, have been subjected to some manner of scholarship, and amongst hardcore fans it is entirely common for a “lesser” work to be their unchallenged favorite. Thus the task of ranking so-called “second tier” Dylan records begins with the not-insubstantial challenge of just what qualifies as such.

For the purposes of this list, we are going to eliminate everything starting from Dylan’s self-titled 1961 debut up through 1969’s Nashville Skyline. This period includes several unimpeachable classics, with world historic influence: the seminal New York acoustic folk album The Freewheeling Bob Dylan; the head-explodingly brilliant trifecta of blues, folk, and rock that made up Bringing It All Back Home, Highway 61 Revisited, and Blonde On Blonde; the stark and stoic response to psychedelia John Wesley Harding; and the aforementioned Nashville Skyline, which essentially invented “insurgent country” two decades before the Mekons and Green On Red stumbled upon it again. This period also includes The Basement Tapes, the legendary 1967 recordings of Dylan and the Band running through new tracks in the basement of their shared home, by turns goofy and harrowing, and utterly un-self-aware. Everything about The Basement Tapes, from its DIY sound to its “fuck it, who cares” first-take spontaneity anticipated much of what would become known as the best of indie-rock.

Dylan was transcendent during this period, but not flawless. A few of the ’60s records might be counted as relatively minor: His debut, Bob Dylan, was composed mostly of (brilliantly rendered) covers and is the sound of a very young man directly on the precipice of finding his own voice. The Times They Are A Changing, his third full-length, represented his deepest identification with the “protest music” whose association he would come to abhor, and a couple of the songs veer toward Joan Baez-style preachiness. Still, with track like “Boots Of Spanish Leather,” “With God On Our Side,” and “The Lonesome Death Of Hattie Carroll,” it is an awesome display of talent, even if it ranks as arguably his seventh best record of the 1960s.

In general, Dylan in the 1960s was too novel, too prolific, and too ingenious to really consider any of these albums minor. Each in their way was a brand new touchstone for understanding the role of popular music in culture, each one its own mirror on our society. Whether the image it displayed was lysergic and surreal, amphetamine-fueled and paranoid, or only too sober in its warts-and-all depiction, there was no more transformative and truth-telling a figure than Bob Dylan during that fractious period in our nation’s history.

It is sometimes more fun as a fan to consider the great artist when they are not firing at the established peak of their powers and clearly struggling with their craft in ways that had not previously been a problem. Dylan himself famously described this process with the indelibly astute comment that getting older meant “learning to do consciously what I used to do unconsciously.” This is exactly true, and exactly what is fun about listening to Dylan’s post-1960s output. At times he has appeared utterly to have lost the muse, to the point it is hard to believe that this is BOB FUCKING DYLAN singing this ridiculous tossaway. Other times he has gathered all of his greatness and brought to bear the additional perspective and life experience to create things as good or better than any of his unimpeachable early masterpieces. Most often, it has been somewhere in the middle: Albums bristle with genius and then apparent ambivalence or failure of will. Great outtakes are left aside for seeming filler. The madness can be incredible, but also incredibly compelling. Our look back at the best of Bob Dylan’s “lesser” work starts here.

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9. Hard Rain (1976): Filmed for broadcast by NBC and performed in a driving Colorado rainstorm, this underrated live album from 1976 is the most enduring document of the second iteration of the legendary Rolling Thunder Revue, the touring circus that Dylan conceived as a way to gather friends and get back to playing smaller venues. Remarkably, for this leg of the tour, Dylan retained none other than recording legend and Ziggy Stardust And The Spiders From Mars guitarist Mick Ronson on lead, bringing a stylistic contrast that informs old standards like "Maggie's Farm" with glam-style energy, and still settles in nicely with quieter fare like Nashville Skyline's poignant lament "I Threw It All Away." Most crushing is a blood-and-guts version of the classic break-up anthem "You're A Big Girl Now," allegedly sung directly to his estranged wife, who had turned up unexpected at the gig, and didn't like everything she saw. Whether the story is apocryphal or true, the depth of pain and rage expressed in the performance is inarguable.

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8. Planet Waves (1974): The curious Planet Waves was billed as a reunion of Dylan and the Band, who had previously -- in various formulations -- turned rock and roll on its head during Dylan's first electric tours. Whatever the reason, the album contains very little of the visceral tension of those early interactions and instead resolves into a largely pleasant, vaguely countrified folk-rock operation that neither offends nor disappoints. Small gems like "Hazel" were later repurposed on the great Band documentary The Last Waltz, and opener "On A Night Like This" manages at once to function as an engaging come-on and something that sounds like a terrible idea. Ultimately, the mean-spirited and spare piano-driven "Dirge" is the most unusual track on the album, one that anticipates the terrible domestic acrimony that would soon be visiting Dylan's life and ultimately coloring the following year's all-time-great Blood On The Tracks. In this context, Planet Waves feels like fascinating insight into a man who seemingly has everything -- a legendary reputation, a loving family, and an estimable fortune -- and is somehow contriving to lose it all.

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7. Pat Garrett & Billy The Kid (1974): Dylan's soundtrack for Sam Peckinpah's 1973 western Pat Garret & Billy The Kid is a spartan, haunting affair, and a strange and transporting listen. For one thing, four of the 10 tracks are different versions of the same song, "Billy," each one sounding a little more stoned and despairing than the last. It is also peppered with instrumentals, some very good, some a little stemwinding. But taken together, the release works startlingly well -- it is deeply atmospheric and doom-laden, autumnal and in certain spots a little frightening. Will Oldham probably should record this entire thing (if he hasn't already). As a sidelight, the most famous track here is "Knocking On Heaven's Door," which has been turned into a horrible classic-rock warhorse by a number of terrible individuals who should probably be prosecuted for what they've done to the poor thing. Here, in it's original conception, it is two and half brief minutes of subtle reckoning with awful mistakes and a life beyond salvation, and surpassingly lovely.

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6. Shot Of Love (1981) and 5. Slow Train Coming (1979): In a career marked by strange and subversive gestures, often seemingly contrived to purposefully wrong-foot his audience, there is perhaps no more shocking episodes then Dylan's public embrace of evangelical Christianity in the late '70s, followed by a trio of overt gospel music. While it is perhaps understandable that many longtime fans would have been dismayed by this development -- especially when he began refusing to play non-religious music at concerts, and also took to some fairly bizarre preaching on stage -- history will also record that this period yielded some of Dylan's greatest songs and indeed some of the greatest devotional music ever written. Unpacking the so-called "Christian period" is in itself a momentous undertaking for which there is not space here, but Slow Train Coming and Shot Of Love are wonderful albums (The second album of spirituals, 1980's Saved, has is moments, but is considerably weaker). Part of the irony of the Dylan-turns-Christian outrage is that a great deal of this music makes perfect sense within the context of his catalog. From the outset he has always littered his writing with scriptural allusion and a restless spiritual striving. In this regard songs like "Slow Train" and "The Groom's Still Waiting At The Altar" are not so different from the early classic songs like "Hard Rain" or "Highway 61 Revisited," both of which function on some level as blues and folk-based biblical parables. Another common misconception is that Dylan had grown scolding and humorless during this period -- this could not be further from the truth. In fact, he often sounds out-and-out giddy, making silly jokes and sounding thoroughly delighted on the enduringly great and insightful "Gotta Serve Somebody." And, finally there is "Every Grain Of Sand," the yearning ballad that closes Shot Of Love. Clearly on a shortlist of his best songs, it is a moving statement of awe and devotion that recalls nothing so much as "Amazing Grace" in its power. Not for nothing was this song performed by Emmylou Harris when Dylan's old buddy Johnny Cash was laid to rest.

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4. Oh Mercy (1989): By 1989, following two mostly terrible albums of originals (Knocked Out Loaded and Down In The Groove) and a lamentable live-album collaboration with the Grateful Dead, it had become, for the first time in nearly three decades, justifiable to wonder if maybe Bob Dylan had nothing left to contribute. At this uncontested career nadir, everything seemed in jeopardy: his health, his reputation, his live shows, and his confidence. Into this predicament stepped the Canadian producer Daniel Lanois, fresh from extraordinary successes with Peter Gabriel and U2, in the latest (and possibly last) attempt to "freshen up" Dylan's sound. At first blush, this would seem to have been a very bad idea, as the gauzy polish and slow-brewing method's signature to Lanois's approach would clash with Dylan's notorious impatience. And indeed, tensions evidently ran high between the two alpha-dogs -- Dylan refers obliquely in his memoir to a fistfight in the parking lot following a session, a profoundly comical image and something that definitely should have happened if it didn't. However, in this instance the tensions between the two seemed to jar something loose in Dylan. Lanois endlessly hectored him to write better songs, and Dylan responded with some absolute gems. "Most Of The Time" and "What Good Am I?" are lovely bits of much-needed self-reflection, whereas other tracks like "Everything Is Broken" and "Political World" are protean versions of the new sound that Dylan would gradually evolve, leading to his unprecedented string of late-career masterpieces. Ironically, the actual production is probably the album's weakest component -- Lanois's insistence on lining the album with his customary atmospherics and sundry U2-isms tends to detract much more from the weight of the material than it adds. Nevertheless, Lanois is due much credit. Under his guidance, and at a crucial stage, he delivered something many people thought they would never hear again: a very good Bob Dylan album. 

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3. Street Legal (1978): The critic Greil Marcus, in his Rolling Stone review of Street Legal, characterized this complicated and frequently brilliant album as "Dylan faking it." In a sense Marcus, who has both provided some of the most crucial and also some of the most myopic scholarship on Dylan's catalog, was correct, but not in the way he imagined. This is deliberately Dylan's showbiz record. Having been a front-and-center observer of Neil Diamond's runaway success, and sharing the same management, Dylan delivers on Street Legal his own particularly demented notion of what a big Vegas run might sound like. Luckily, he couldn't find schmaltz with a Geiger counter and what results is one of the strangest hybrids ever committed to record: densely layered songs ladled with sundry horns and wailing backing singers. All of these crowd the legendarily poor and slapdash mix (which was remastered to great effect in 1999) and ultimately make for a challenging and claustrophobic listening experience, something like Elvis Costello's similarly crazed Punch The Clock. Still, Street Legal contains no shortage of brilliant material, and its enigma and quality only gain currency over time. Amongst its other charms, the opening track, music-business allegory "Changing Of The Guards," brimming with mysterious allusions, unforgettable turns of phrase, and regular saxophone breaks, is clearly the greatest proto-Dan Bejar song ever written.

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2. Infidels (1983): Dylan's brilliant, idiosyncratic 1983 album, Infidels, is a rich tapestry of spiritual seeking, social commentary, and sly humor. Backed by a killer band including reggae legends Sly & Robbie as the rhythm section, and former Rolling Stone Mick Taylor on guitar, Dylan is feeling apocalyptic here. The enchanting, image-laden "Jokerman" is a full of fear and wonderment, while 
"Neighborhood Bully" and "Man Of Peace" are blues-driven tours through the war-torn Middle East as frighteningly relevant today as they were at the time. The great mystery of Infidels remains Dylan's decision to leave off two wonderful tracks that, if they had been included, might have elevated the album to the heights of his greatest achievements. "Foot Of Pride" features a punishing groove punctuated with an archly comic set of lyrics, forecasting mankind's downfall by dint of its own vanity. Meanwhile, the shattering "Blind Willie McTell" is one of the single most beautiful songs he has ever written, a panoramic love letter to the titular blues legend, which also ponders with great sorrow a world seemingly spiraling inextricably toward doom: "Seen the arrow on the doorpost / saying this land is condemned / All the way from New Orleans / To Jerusalem."

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1. New Morning (1970): Having worn himself to the very edges of mortality, in the early '70s, Dylan drew back both personally and artistically, making the great concentration of his life and work the seemingly idyllic home that he kept with his first wife Sara Lownds and their children. New Morning was a charming, by-the-books account of domestic equanimity -- the artist at his most sanguine and comfortable. The loose feel of the Bob Johnston-produced album represented a kind of full-fledged departure from the "songwriter of a generation" and exemplified very much the discomfort of a flesh-and-blood individual who had passed somewhat inadvertently into mythology. Great songs abound, from the gorgeous opening anthem of permanent love "If Not For You" to the who-doesn't-enjoy-the-credit-sequence-in-The Big Lebowski "The Man In Me." On balance, it's one of Dylan's most successful and underrated records.

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