A CityLab guide to the Dylan canon and the allure of the city.

Never mind whether Bob Dylan’s lyrics qualify as Nobel-worthy literature. Here’s the real question: Is he an urbanist?

A lot of the urbanist internet sure thinks so. In its subterranean realms you’ll find maps of Bob Dylan’s New York, a list by CityLab alum Eric Jaffe on Dylan’s best songs about infrastructure, and an English paper about his quality as an urban poet.

Another tidbit: a count of mentions for each mode of transportation in the Dylan canon.

Bob Dylan: kind of a train geek but mostly a fan of walkability. (Charlie Gardner/Old Urbanist)

There’s also a map of every place mentioned in a Dylan song. CityLab has previously reported on the geography of his Neverending Tour and his possible songwriting collaboration with Jane Jacobs, perhaps the most coveted of all possible urbanist achievement badges.

Dylan and friend explore a dense, walkable, mixed-use neighborhood. (Columbia Records)

Of course, Dylan’s main claim to urbanism fame stems from his status as an archetypal New York transplant. The cover of his second album, The Freewheelin’ Bob Dylan, now evokes nostalgia for the bohemian era of Greenwich Village folkies in coffeeshops. The New York Times quotes Suze Rotolo, Dylan’s girlfriend on the Freewheelin’ cover, to demonstrate his complicated but romantic relationship to the city.

“In those early years Bob Dylan was a painter searching for his palette,” Ms. Rotolo, an artist who died in 2011, wrote in “A Freewheelin’ Time: A Memoir of Greenwich Villages in the Sixties.” “He had in mind the pictures he wanted to paint; he just needed to find the right color mix to get him there.”

He also, she wrote, “had an uncanny ability to complicate the obvious and sanctify the banal — just like a poet.”

So New York played the part of a muse for Dylan—in hard times and in better ones. And yet, it wouldn’t be Bob Dylan if there wasn’t still a mystery, a contradiction, an ambivalence. His post-protest career has always made him a bit of a Rorschach test. To the left, his abandonment of conventional politics was part of the tradition of broader American cultural progress. To the right, his retreat from protest songwriting was individualistic, or even reactionary. He’s similarly enigmatic with his attitude about the city.

In his memoir, Chronicles, Volume One, Dylan writes that “New York was a city where you could be frozen to death in the midst of a busy street and nobody would notice”—this from a guy who wore a thin jacket when it was freezing out to look cool on his album cover. But I would try not to overthink it too much.

I’ll also avoid dragging you through stanzas of Dylanography that highlight his enigmatic takes on great urban themes or tracing every city in his overexposed biography (though I’ll highlight Nashville as a necessary antecedent to New York). Instead, here’s a playlist of his best CityJams; listen and decide for yourself. Don’t follow leaders and watch the parking meters!

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