Bob Dylan at 80: Chronicling Dylan’s Greatest Misses

In a career begun almost sixty years ago with the release of his eponymous debut album, Bob Dylan may well have alienated listeners as often as he’s enticed them. Nevertheless, his status as a cultural icon is hardly in question:  the mere mention of his name invariably elicits a response even if it’s not always a positive one – and how many impersonations of his oft-caricatured vocal style have you heard?

Even accusations of plagiarism in recent years have done little if anything to undermine his achievements (the furor over rewarding him a Nobel Prize notwithstanding) and as the man turns 80 on 5/24/21. That perspective brings an unusual clarity to the ongoing evolution of his work. Of course, within an extended chronology where more than a few distinct periods emerge, Bob has rarely catered to expectation; he much prefers following his instincts, during which process it seems he often doesn’t think twice about the response. Herewith, two handfuls of those confounding instances wherein The Bard of Minnesota lived up to his reputation solely on his own terms and not anyone else’s.

Live Albums


At Budokan (1979)

In keeping with the pseudo-Elvis attire in which he’s pictured on the cover (a replay of the photo on the back of his previous album Street Legal), there are glossy arrangements like that for “Blowin’ in the Wind,” rendered by the large(r) band that appeared on the aforementioned 1978 studio effort, calculated to appeal to the lowest common denominator. It’s an approach Dylan has rarely taken otherwise, except (somewhat ironically) when he reunited with his most sympathetic accompanists, The Band: for the mega-tour of 1974, setlists varied only slightly more often than the format of the shows. At least then, however, Bob was aiming first at his devoted fan-base and then at the merely curious mainstream public.

In an instance of circular logic, this crowd-pleasing (sic) from the Far East–eviscerated by many critics and followers–preceded Bob’s decision not to play any vintage material at all on his initial tours during the born-again phase soon to commence.


Dylan & the Dead (1989)

Multiple recordings of even more scintillating song choices, as well as galvanizing performances, appear in bootleg form distinctly superior to this pro forma outing. Seemingly released only because it would’ve been remiss not to do so, the seven tracks don’t evince the careful thought applied to their selection, production, and packaging as had become de rigueur by this time with live Grateful Dead recordings such as those of the Dick’s Picks archive series.

More disappointing still, the performances don’t radiate much of that spark of rediscovery that Jerry Garcia took great pains to instill in Dylan early on in preparations for touring together (at least according to various accounts including the principals’, the titular leader of the Dead took great pains to remind the groundbreaking songwriter how so much of his vintage material was supposed to go).

Perhaps this collaborative project planted that seed for the self-professed epiphany Dylan experienced on stage in Switzerland later that year and if that is indeed the case, it may also be the worthwhile means to the greater end of regular roadwork: initially dubbed ‘The Never-Ending Tour, much of what followed has been rife with surprise (Neil Young and Warren Zevon covers!?!) right up through 2019. 


The Bootleg Series Vol. 4: Bob Dylan Live 1966, The “Royal Albert Hall” Concert (1998)

Myth-making in action here, certainly not myth-busting. Ostensibly issued to clarify once and for all the mystery surrounding one of the most famous bootlegs of all time, the double-disc package only ended up whetting the appetite for more from this same tumultuous tour with the Hawks, nee The Band. Reparations would arrive eighteen years later in the form of 2016’s thirty-six CD box set The 1966 Live Recordings: the comprehensive collection of purportedly all authorized recordings from this fateful world trek thus render its predecessor virtually the definition of anticlimactic. Remaining readily available commercially and sporting the notable presence of italics in the title suggested the release nevertheless represented an acknowledgment of history the likes of which Bob Dylan has rarely been inclined to indulge, even in the wake of the 1991 initiation of this archive series. 

Studio Albums


Knocked-Out Loaded (1996)

Released near the end of Dylan’s first round of touring with Tom Petty and the Heartbreakers, fans, as well as dilettantes alike, might have reasonably expected either a representative live album or studio work with some of the punch and unpredictability of the stage show (a Rolling Stone Magazine feature of the time suggested the latter was in fact in the works).

Instead, Dylan delivered one of the weakest pieces of work in his discography, highlighted (if that’s the right word) by the eleven-minutes plus of  “Brownsville Girl.” To make matters worse, this overlong quasi-recitation, composed with playwright Sam Shepard, is surrounded by as more cover material and collaborative songwriting efforts than Dylan wrote by himself. Per the man’s own observations, he gave this work little attention during recording because he didn’t expect any album of his to get much attention; this turned out to be just one of a number of instances Dylan acted on that attitude during this era, leaving (reaffirming?) the distinct impression he’d prefer little or no attention except that which was absolutely required of him (or requested by him) as a public figure.

Self Portrait (1970)

Rarely has a major artist’s work caused so much consternation over so long a period of time, not to mention the almost directly proportional rethinking and revisionism as well. Savaged by many critics and fans in its original form at the time of its 1970 release, it was the 2013 issue of The Bootleg Series Vol. 10: Another Self Portrait (1969–1971) that put the stylistic diversity collected on four sides of vinyl into the proper context: Bob Dylan’s attempt to re-ignite his own inspiration to compose new original songs by a thorough examination of the roots of his music. Yet that historical revamp came years after Bob’s only thinly-veiled commentary on the contrary premise by which he first put the record out: to deliberately alienate a loyal following that refused to acknowledge his abdication of cultural leadership following his self-imposed hiatus in the wake of the famous (alleged?) motorcycle accident in 1966.

Infidels (1983)

One of the most polished and well-played studio efforts of Dylan’s career to that point, this LP completed Bob’s exit from the religious phase of his career began on the informal-to-a-fault Shot of Love from 1981. Certainly, it compared favorably to the previous production high point, the Jerry Wexler-supervised Slow Train Coming of 1979 and, perhaps not coincidentally, a participant in the latter effort, Dire Straits’ Mark Knopfler, co-produced this project with Bob himself—at least to the point the guitarist/songwriter left to tour with his own band.

Under those seemingly ill-planned circumstances—illuminated to some degree but not completely in Terry Gans’ book Surviving In A Ruthless World: Bob Dylan’s Voyage to Infidels—Dylan took it upon himself to reconfigure the tentative tracklisting. Thus, at least one certifiably great song, “Blind Willie McTell,” was absent when the modified collection was issued, with the markedly inferior ”Union Sundown” part of a track-listing that would’ve benefited tremendously from other session outtakes (like “Foot of Pride,” notably included on the initial volume of The Bootleg Series).

Empire Burlesque (1985)

“Dark Eyes” and “When The Night Comes Falling” represent the two ends of an artistic spectrum Dylan established two decades before with his acoustic/electric roadwork with the Band, nee the Hawks (formerly backup to Ronnie Hawkins). Untarnished by Arthur Baker’s au courant disco-oriented mixing style, both the haunting former solo piece and the latter full-tilt rocker—in its more streamlined form as included on The Bootleg Series Volumes 1-3 (Rare & Unreleased) 1961-1991—remind that the fault in Dylan’s recordings of this era lie less in the quality of material than that of the production values (at least in this case, with some discernible overflow of songs from the preceding project).

Under The Red Sky (1990)

This is one of, if not the most, utterly conventional albums of original songs Bob Dylan has ever released. And that’s being kind, in part because it represents such a precipitous drop off from the remarkable return to form that was 1989’s Daniel Lanois-produced Oh Mercy (released almost a year to the day prior). Chalk it up to the hurry to meet other commitments or Bob’s relative recurring disinterest with the recording process, but the presence of so many guest musicians only lends credence to the theory their presence was simply the means to provide compensatory selling points for a record that had few of its own, if any, apart from the artist’s name on the cover.

Producer Don Was (who was yet to ascend to his subsequent position of prominence at Blue Note Records or assume his role as studio collaborator with The Rolling Stones) may or may not be responsible for the wayward marketing angle represented by appearances from the disparate likes of Bruce Hornsby, Elton John, and George Harrison. But, the fact of the matter is, those esteemed figures’ contributions don’t serve the artist well or redeem songs like “Wiggle Wiggle” or “Cat’s In the Well” (later described by the author as intentionally composed as children’s songs).

Together Thru Life (2009)

One of the first self-productions Dylan took upon himself under the assumed name ‘Jack Frost” qualifies as a learning opportunity, this despite the fact most of the material was co-written by the Nobel Laureate with the Grateful Dead’s brilliant wordsmith Robert Hunter. Few of the lyrics ascend to either man’s customary brilliance, while the arrangements and audio mix highlight the accordion of Los Lobos’ David Hidalgo over the electric guitar of Tom Petty’s most regular collaborator, Heartbreaker Mike Campbell.

What’s even more enervating is that in those instances when both of the latter are playing their main axe, they’re not afforded much leeway to improvise on their own or interact with each other; such an open-ended approach, in which both men have proven they excel, might’ve redeemed a record that otherwise ends up an especially frustrating exercise in futility, based on the legitimately elevated expectations of the collaboration(s).

Shadows in the Night; Fallen Angels; Triplicate (2015, 2016, 2017)

Over the course of approximately three years, Bob Dylan clearly took his explorations of the ‘Great American Songbook’ quite seriously. Not surprisingly, for that reason alone, the arrangements, production, and performances–largely live in the studio by Dylan’s road band, with some horns and orchestration added on–were all of the comparably high quality.

Yet what was unquestionably more startling than the extent to which Bob pursued his interest in such material (even performing it regularly in concert) was how clear his voice rang as he sang: delivery so fastidiously-phrased on tunes such as “Stardust” and “As Time Goes By” gave the lie to accusations the man’s voice was shot. The elevated level of engagement in Dylan’s performances almost made a devotee forget these recordings followed so long after his last collection of original material, the superb Tempest of 2012 (and may have forestalled the next one. 2020’s Rough And Rowdy Ways).

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