The 10 Best More-Obscure Bob Dylan Albums

10. Empire Burlesque (1985): A major narrative thread of Dylan’s career through the early to mid ’80s was his label’s peculiar and particularly ill-judged obsession to give the man a more “contemporary” sound. Dylan himself seemed to recognize this was fundamentally not a good idea, and resisted or at least complained about it, but as an aging rock star with fading commercial prospects, he acceded to a number of collaborations with label-approved producers in order to make him sound more like Johnny Cougar or Huey Lewis, or something. The nadir of these mismatches came on 1985’s Empire Burlesque — a release helmed by Arthur Baker. Baker was a minted industry hand whose resume included mixing and recording work with New Order and Cyndi Lauper, amongst others. The sessions went on interminably, and one imagines Dylan, who famously prefers to cut things quickly and with great spontaneity, growing gradually more insane. In fairness, one also imagines Arthur Baker going insane as well, tasked with forcing a cranky legend into making a “contemporary” sounding record over his objections. Anyway: The thing sounds insane, completely mad. But through the dense layers of ’80s production touches and weird “trying to find a hit” arrangements, there are a bunch of pretty great songs. “Dark Eyes” is one of his loveliest ballads, and remains a fan favorite, even in this iteration. “When The Night Comes Falling From The Sky” is an ambitious and powerful piece of writing, recorded to much better effect on a version backed by the E Street Band which was later released on The Bootleg Series Vol. 1. Empire Burlesque can be a lot of fun, in its way, as an exercise of imagining what this might have been like had it been recorded during the era of what Dylan nostalgically refers to as “live studio excitement.”

The 10 Best More-Obscure Bob Dylan Albums

10. Empire Burlesque (1985): A major narrative thread of Dylan’s career through the early to mid ’80s was his label’s peculiar and particularly ill-judged obsession to give the man a more “contemporary” sound. Dylan himself seemed to recognize this was fundamentally not a good idea, and resisted or at least complained about it, but as an aging rock star with fading commercial prospects, he acceded to a number of collaborations with label-approved producers in order to make him sound more like Johnny Cougar or Huey Lewis, or something. The nadir of these mismatches came on 1985’s Empire Burlesque — a release helmed by Arthur Baker. Baker was a minted industry hand whose resume included mixing and recording work with New Order and Cyndi Lauper, amongst others. The sessions went on interminably, and one imagines Dylan, who famously prefers to cut things quickly and with great spontaneity, growing gradually more insane. In fairness, one also imagines Arthur Baker going insane as well, tasked with forcing a cranky legend into making a “contemporary” sounding record over his objections. Anyway: The thing sounds insane, completely mad. But through the dense layers of ’80s production touches and weird “trying to find a hit” arrangements, there are a bunch of pretty great songs. “Dark Eyes” is one of his loveliest ballads, and remains a fan favorite, even in this iteration. “When The Night Comes Falling From The Sky” is an ambitious and powerful piece of writing, recorded to much better effect on a version backed by the E Street Band which was later released on The Bootleg Series Vol. 1. Empire Burlesque can be a lot of fun, in its way, as an exercise of imagining what this might have been like had it been recorded during the era of what Dylan nostalgically refers to as “live studio excitement.”

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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