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Every Bob Dylan Album Cover Ranked

Some are iconic images that changed rock, others make you wonder “What was he thinking?”

Even before he had a record contract, Bob Dylan was thinking about his visual presentation. Folk singer Dave Van Ronk advised him that he needed to think about his image, Dylan’s girlfriend Suze Rotolo wrote in her 2008 memoir, A Freewheelin’ Time: “Much time was spent in front of the mirror trying on one wrinkled article of clothing after another until it all came together to look as if Bob had just gotten up and thrown something on. Image was all.”

So come gather ‘round, people, and let’s judge Dylan by his image, or his images. We’re ranking all 40 of his studio albums by the quality of the cover art. We’ve left out archival discs like the Bootleg Series and hits collections: It’s relatively easy to pick a stellar cover with years of perspective, but we want to know how Dylan chose to present himself to the public in real time. Sometimes Dylan made iconic covers, both calculated and spontaneous; sometimes he treated them with the same regard as a grocery list. 

Some of the worst covers, however, reveal his lifelong obsession with masks and costumes, like Einstein disguised as Robin Hood. Dylan could stare a camera down and win, but often he preferred to be masked and anonymous. “It’s one thing facing a writer,” he said to a New York Daily News reporter in 1967, “but I have this hang-up about cameras now.”

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