Bob Dylan's Best and Worst Album Covers

Musical Genius, Yes. Skilled Creator of Cover Art? Sometimes.

By Jay Michaelson

Published October 02, 2012, issue of October 05, 2012.
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My relationship with Bob Dylan is similar to my relationship with Woody Allen: I’m a fan of these old Jewish guys, and I get excited when a new release is announced. Even after “Knocked Out Loaded,” even after the film “Celebrity,” I keep the faith — and when I’m treated to a “Time Out of Mind” or a “Midnight in Paris,” it’s as if my steadfastness has been rewarded.

In this context, album covers and film posters (or their digital equivalents) become deeply important. What do they reveal? What do they say about this next project from the old master? And will it be any good?

It was thus with dismay that I first gazed upon the cover of Dylan’s new release, “Tempest,” which came out on September 11. It is, in my opinion, the worst Dylan cover ever — and there have been some doozies over the years. Fortunately, the songs on “Tempest” are actually quite good late-model Dylan, complete with retro stylings, apocalyptic pronouncements, bar-band messiness and biblical allusions. But the tossed-off nature of the cover has led me to muse on Dylan covers past and present, and to compile this highly idiosyncratic list, counting down the five best and five worst album covers from the bard’s 50-year career.

The Best

5. Slow Train Coming (1979)

Jewish fans of Dylan may despise this album, the first of Dylan’s short stint as a born again Christian. But the cover, with its subtle cross symbolism, vision of redemption and home-grown feel, perfectly captures Dylan’s spiritual renaissance after a few years of drug and alcohol addiction — itself well captured on the cover of his previous album, “Bob Dylan at Budokan.” Like “John Wesley Harding,” which it narrowly beat out for the No. 5 spot, the cover of “Slow Train” is at once enigmatic and revealing. You want to know more.


4. World Gone Wrong (1993)

This cover is the first time we really saw the Dylan who now has been with us for 20 years: a grizzled old singer of traditional songs that pack emotional wallops behind deceptively simple facades (the songs here are all traditional folksongs, performed by Dylan and accompanied only by his own guitar and harmonica). Seated in front of one of his own paintings, Dylan isn’t hiding his age here — quite the contrary. He wrote in the first volume of his quasi-memoir, “Chronicles,” that he realized that in order to do these songs justice, he’d have to become a new man entirely. That man is pictured on the cover.


3. Greatest Hits (1967)

Few remember today that Dylan’s first several albums, now classics, were not commercial successes. It was only after the electric period that his early work became known — and that, in large part, was because of this collection. The cover shot is iconic, situating Dylan right in the center of the 1960s, his profile backlit and his hair as if on fire. This Dylan would flicker out of existence only a few months later, to be replaced by the country crooner of his next few releases. But for a moment, electric Dylan was it.


2. Bringing It All Back Home (1965)

This is probably the most enigmatic Dylan cover of all. The image on the sleeve of “BIABH” signaled a rejection of Dylan’s protest-singer past and a new phase of creativity and complexity. Who is the woman in the background? What is the significance of the magazines on the table? Dylanologists have puzzled over these questions for decades. But this album, in its music and its cover art, was the first indication that Dylan would not conform to expectations and would instead surprise and mystify.


1. The Freewheelin’ Bob Dylan (1963)

Some images are just icons, and this cover is one of them. Capturing the youth and potential of the early 1960s, Dylan and his girlfriend, Suze Rotolo, huddle against each other as they walk down a New York street. They are cold, they are poor, they are young and they are happy. No wonder this image has been copied and parroted so many times (see, for instance, Cameron Crowe’s Tom Cruise flick “Vanilla Sky”): Is there a more iconic image of bohemian youth than this one?

Honorable mentions: “John Wesley Harding,” “Oh Mercy,”“Dylan & the Dead,” “Blood on the Tracks,” “The Basement Tapes.”


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