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.