The Freewheelin’ Bob Dylan

I remember my first real taste of Bob Dylan. My final year of high school saw me extremely anxious and desperate to see an end to its cyclic, repetitive nature. On a rainy day in October, out of sheer impulse, I decided it far more reasonable to visit the Met and wander about the East Side than to sit in a classroom for seven hours. The seemingly out of place emptiness of the rainy city eerily reflected my inner feelings, and as I sat emotionally drained at a Two Boots’ Pizza off of Lexington, I heard the electric bluesy “Ballad of a Thin Man” and was instantly mystified by its wit and obscurity. Dylan, to me, will always represent a sense of nostalgia and despondency, but his music arguably embodies so much more than that. As a folksy songwriter who came into his own in an era of social unrest, Dylan’s legacy lies in his political commentary and sense of surrealist humor. Dylan’s artistry not only shaped the folk scene of the West Side, his music proved to be instrumental in contributing to the narrative of the political, left-wing activism that resisted war, greed, and civil inequalities during the 60s.

Bob Dylan pictured in 1963.

Bob Dylan is an artist memorialized by his distinct and various musical sounds, by his sharp wit and mysteriously crafted persona, and by his constant breaking of boundaries, for well over the course of half a century. At the start of his revolutionary career lies a humbler Dylan with a keen, young voice that sings of rejection towards a retrogressive government. The West Village’s Bob Dylan was born the far less glamorous Robert Allen Zimmerman in Minnesota. Nearly twenty years later, Dylan skipped town and moved in with his girlfriend, Suze Rotolo, and her radical left-wing parents in New York City. Dylan’s intention in moving to the city, other than to launch a career, was to meet his musical hero, folk artist Woody Guthrie, whose music he applauded as having “the infinite sweep of humanity in them.” Guthrie, to Dylan, “was the true voice of the American spirit” and he longed to become “Guthrie’s greatest disciple.” As Dylan began to establish a name for himself by playing small gigs in the West Village, particularly at local club Cafe Wha?, he visited Guthrie in the hospital, fulfilling his goal to meet and establish a relationship with the folk icon. New York proved to facilitate Dylan’s goals even further when he was signed to Columbia Records and produced his first album, a self-titled collection of mostly covers and two original songs. Bob Dylan was far from a hit, selling only 5,000 copies in its first year, but his unique sound and quirk drew the attention of many. His 1963 sophomore album, The Freewheelin’ Bob Dylan,  proved to be a far more successful, selling 10,000 copies per month.

Cafe Wha? pictured in 2016, located on Macdougal St in the West Village.
Album art featuring Bob Dylan and Suze Rotolo on Jones St and West 4th St.
Recreated album art featuring Julia Brennan and Zoe Fanzo (on the same street, five decades later).

The Freewheelin’ Bob Dylan, as most folk music of the time, was a response to civil unrest and injustices, heavy in the mind of Dylan. His youthful perspective on the relevant issues of the day resonated with Americans to an unexpected and unprecedented extent. Folk, far from mainstream and fairly underground at the time, was recalled by NPR as being “completely unlike anything else on the radio, which at the time was dominated by highly produced pop songs.” Folk became a means of political commentary for Dylan, and quickly ascended him to a platform he did not anticipate; “Spokesman of a Generation.” To Dylan, the rapidly accumulating collegiate cult following was not particularly unwelcome, but the rising media presence in his life was entirely detested. Whereas he was passionate about the words he was singing and the music he was playing, his work was exploited by the media and his image distorted. Recalled in his autobiography, “The press never let up. Once in awhile I would have to rise up and offer myself for an interview so they wouldn’t beat the door down. Later an article would hit the streets with the headline ‘Spokesman Denies That He’s A Spokesman.’ I felt like a piece of meat that someone had thrown to the dog.” Despite the nuisance of a media presence, Dylan continued to gain a cult following, segwaying him into a career of cultural complexity.

“Blowin’ in the Wind,” the album’s opening track, is regarded by Rolling Stone as being the 14th greatest song of all time– “Like A Rolling Stone,” a later Dylan piece, being dubbed the absolute greatest and, incidentally, one namesake of the popular music magazine– and the “most famous protest song ever written.” The social impact that “Blowin’ in the Wind” is almost too tremendous to fully grasp so many decades later, but during the Civil Rights Era, it was an anthem. “Blowin’ in the Wind” was covered by an extensive array of artists of all genres, being performed by Peter, Paul, & Mary at the March on Washington for Jobs and Freedom, by Peter Yarrow at the March from Selma to Montgomery, and by Dylan himself at a voter registration rally in Mississippi. To many, the appeal of the song is its ambivalence, its lack of answers. What “Blowin’ in the Wind” offered, oppositely to most topical protest songs of the time, were no absolutes. It did not speak of specifics, it only played upon the emotions and conscious of its audience in order to impose purpose.

Altogether, Freewheelin’ transformed the folk scene, bringing the genre further into the mainstream, as it appealed to young, disillusioned Americans. Dylan essentially brought folk and politically involved youth together, bridging the gap between them. Just as his folk narrative began to take flight, Dylan shifted his sound in the mid-1960s. Dylan, simply put, felt constrained by the folk sound. The widespread association of Dylan with “protest songs” molded him into a one-dimensional artist, something that his creativity would not allow for. Bringing It All Back Home, his 1965 album, incorporated the use of electric instruments, and though it was not entirely electronic, considering “Mr. Tambourine Man” was one of the album’s most popular acoustic tracks, it was rejected by the folk purists who made up a great deal of his fanbase. “Mr. Tambourine Man” was acoustic and reminiscent of the folk genre, but the song itself encapsulated Dylan’s shift in vision; it was not topical, nor was it a protest song. In 1965, at the Newport Folk Festival, which he played two times before to a wholly positive reception, he was booed off stage for deviating from traditional folk. Mojo Magazine recalls, “Dylan had stood music on its head by playing folk-style, writing about politics and making hits. For which many came to depend on him. Then he changed. He got loud and wrote about emotions, relationships, wild things beyond rationality, ideals and good intentions. And so, ‘Judas!'”

[An example of Dylan’s electric sound]

Change was not received lightly by the folk purists, but Dylan’s multi-dimensionality could not be curbed. Nat Hentoff has said of Freewheelin’, “This album, in sum, is the protean Bob Dylan as of the time of the recording. By the next recording, there will be more new songs and insights and experiences.” The heavily political album was a direct reaction to the time it was created, but as he began to feel the pressure of being labeled the “Spokesman of a Generation,” and as the tides of political unrest grew stronger, a change in style became an inevitability for Dylan. Though Dylan continued to produce what he recognized as protest songs, they became less topical and more vague, angering folk purist fans that he had accumulated with Freewheelin’. As an artist, it was his desire to branch out and avoid being confined, but anti-Vietnam protestors yearned for a more familiar Dylan.

The Freewheelin’ Bob Dylan is important to more than just the civil rights narrative of the 1960s. As Dylan’s first hit album, it launched his name into household recognition and brought a political awareness to a generation of disconnected youth. It single-handedly launched Dylan’s career, and it served as a climactic moment of personal evolution. It was the response to Freewheelin’ and the unwelcome worship and desire to brand him as a generational voice that crucially influenced his musical transformation, and reinvented Dylan as a multi-faceted musician, essentially into the Dylan that we presently acknowledge as being one of the greatest American artists. It can be safely said that The Freewheelin’ Bob Dylan captures the moment in which Dylan transformed from a low key Village gig player into a global phenomenon and artist of an era, making it one of his most important compositions, and one of New York City’s many genuine masterpieces.

Bob Dylan pictured in 1963.

A few suggested readings…

Chronicles: Volume One by Bob Dylan

“The Politics of Bob Dylan” by Mike Marqusee

“‘Blowin’ In The Wind’ Still Asks The Hard Questions” by Brian Naylor

“Bob Dylan In The ’60s” by Phil Sutcliffe 


Written by Zoe Fanzo (who is looking forward to seeing Dylan in concert at Forest Hills Stadium this July)

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