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American singer-songwriter, author, and visual artist Bob Dylan In Massachusetts, April 1964. (Photo by John Byrne Cooke Estate/Getty Images)
Sixty years ago Bob Dylan changed music forever

Sixty years ago Bob Dylan changed music forever

American singer-songwriter, author, and visual artist Bob Dylan In Massachusetts, April 1964. (Photo by John Byrne Cooke Estate/Getty Images)

Liz Thomson looks at the cultural legacy of The Freewheelin’ Bob Dylan – and how it intersects with the artist’s own contradictory image

Sixty years ago this May Bob Dylan released his second album, The Freewheelin’ Bob Dylan. That summer 250,000 people marched on Washington to demonstrate that in 1963 black lives mattered. Dylan himself sang from the steps of the Lincoln Memorial as Dr Martin Luther King spoke of his dream.

Dylan always insisted that he never wanted to be a spokesman for his generation but his silence during America’s recent agonies seems shameful. And he has been almost as silent on an issue last year that will stain his reputation – the use of an autopen on a high-price, limited “signed” edition of his book, The Philosophy of Modern Song, and on unspecified “signed” artwork.

Dylan claimed to have been ill-advised, to have made “an error of judgement” in the face of a looming deadline while suffering from vertigo. Both his publisher and his art gallery have declared that they were unaware of Dylan’s use of an automated signing device. Yet the question remains: who knew what and when? Money has had to be refunded to fans who bought items assuming Dylan had signed them himself. It’s the sort of scam the angry young Dylan might have turned into a song, one of his sardonic talking blues.

In recent years, Dylan has helped advertise banks, cars and even lingerie. That seemed merely crass and commercial. Now he appears greedy and duplicitous.

The “iconic” cover of The Freewheelin’ Bob Dylan from 1963. Main image above, Dylan in Massachusetts, April 1964

The cover of The Freewheelin’ Bob Dylan, that first appeared in May 1963, is worthy of that often misused word “iconic”. It has come to “signify” so much more than was imagined (much less intended) when the Columbia Records photographer Don Hunstein arrived at a tiny walk-up apartment at 161 West 4th Street (above Bruno’s Spaghetti Shop) in Greenwich Village where Dylan and Suze Rotolo were paying $60 a month to live.

After taking a few frames of Dylan seated in a ratty old armchair that had been rescued from the sidewalk, it seemed a good idea to venture into the slush and frigid cold of Jones Street. The inadequately dressed young lovers huddled together for warmth as Hunstein clicked away.

Rotolo recalled that Dylan “chose his rumpled clothes carefully”, but the image was created on the fly, without recourse to make-up artists and stylists, and it broke the mould. “It is one of those cultural markers that influenced the look of album covers precisely because of its casual down-home spontaneity and sensibility,” wrote Rotolo in her affecting memoir A Freewheelin’ Time (2008).

That image has been widely imitated – Fred Neil at the crossroads of Bleecker and MacDougal; Simon and Garfunkel on the 5th Avenue–53rd Street subway, the Ramones on the Bowery, the Beatles on Abbey Road – but few musicians allowed their girlfriends to share centre-stage. Rotolo, who died in 2011, was the subject (or object) of two of the record’s songs and as someone steeped in social and political action there’s no doubt that she had helped shape his world view. Perhaps Hunstein intuited all that when he suggested she be in the picture.

“Dylan always insisted that he never wanted to be a spokesman for his generation but his silence during America’s recent agonies seems shameful.”

Dylan himself told friends the cover was the most important part of the album but he was wrong about that. His first record, Bob Dylan, released the year before, had sunk almost without trace. Only two of its 13 songs had been written by him. By contrast, 11 of the songs on Freewheelin’ were his compositions, including some of the most significant. ‘Blowin’ in the Wind’ was followed by two of Dylan’s other most celebrated protest offerings, “Masters of War” and ‘A Hard Rain’s a-Gonna Fall’, as well as one of his most enduring love songs, ‘Girl from the North Country’, and anti-love songs, ‘Don’t Think Twice, It’s All Right’ (about or to Rotolo).

Peter, Paul and Mary released their version of ‘Blowin’ in the Wind’ the month after the album’s release. Within a week it had sold 300,000 copies, peaking at number two on the Billboard chart and 13 in the UK, and ultimately selling more than a million copies.

It earned the then impoverished young singer-songwriter $5,000 – a result of manager Albert Grossman’s tactical business planning: the ever-wily impresario handled both acts and the publishing deal gave him 50 per cent of Dylan’s earnings as a composer on top of the 25 per cent management fee he charged all his artists at a time when the going rate was 15.

Dylan came to feel abused by Grossman and their break in 1970 was bitter, but his conduct in recent years suggests the financial lessons of those early years weren’t lost on him.

Dylan with his manager, Albert Grossman, in Denmark in 1966

Dylan had arrived in New York a little over two years earlier, a drop-out from the University of Minnesota fixated on Woody Guthrie and determined to meet the Dust Bowl balladeer whom Huntington’s chorea had condemned to a living death. A folk revival was sweeping the country and Dylan headed to Greenwich Village, where he joined scores of young hopefuls scuffling for dimes on the rickety stages of the clubs around Washington Square.

In September, he was opening for the Greenbriar Boys, a respected bluegrass trio at Gerde’s Folk City. The New York Times critic, Robert Shelton, was in the audience. His review, which ran on 29 September 1961, described Dylan as “one of the most distinctive stylists to play a Manhattan cabaret in months”, his work bearing “the mark of originality and inspiration” that was “all the more noteworthy for his youth”. Fellow critics and many musicians – some of whom regarded the young singer as a joke – were perplexed.

Bob Dylan and John Hammond, at Columbia Studio in New York, 1961

Within a few days, John Hammond, Columbia Records’s renowned A&R man and producer, had offered Dylan a contract. Rotolo remembered the moment as “over-the-top exciting”, writing: “Robert Shelton had been around the clubs and bars for ages, seeing every new and old performer, but he’d never written a review quite like the one he wrote for Bobby…”

Bob Dylan had been recorded over three afternoons in November 1961. Released in March 1962, it received little critical attention and sales were so lacklustre that Dylan was dubbed “Hammond’s Folly”. As Shelton writes in his biography No Direction Home: The Life and Music of Bob Dylan, originally published in 1986: “The first album was the last will and testament of one Dylan and the birth of a new Dylan.”

Shelton was perspicacious, hearing that night what many others did not. His judgement was borne out with the release of Freewheelin’, which marked Dylan’s debut as a fully fledged songwriter. Recorded in sessions spanning July 1962 to April 1963, it was indeed a rebirth, light years away from what had gone before. Robert Allen Zimmerman, as he had once been known, had taken poetry off the bookshelves, paired it with melodies of folk-like simplicity accompanied by guitar and harmonica, and loaded it on to the jukebox.

Dylan, 21, plays a London pub, 1962

The Freewheelin’ Bob Dylan launched the era of the singer-songwriter, closing the book on Tin Pan Alley and the songwriting industry that had turned out hits good, bad and indifferent for decades. The tra-la-la days of the gilded Brill Building, where the likes of Leiber and Stoller, Bacharach and David, and Goffin and King had plied their trade – referred to in Dylan’s spoken introduction to ‘Bob Dylan’s Blues’ – were over.

In Britain, the Beatles had just released their debut LP, Please Please Me. Eight of its 14 tracks were originals, seen as audacious at the time. So too with their second, With the Beatles, which dropped in November 1963, much the same time as Freewheelin’ hit British record stores.

The country was in the grip of Beatlemania following the group’s celebrated appearance on the peak-time television show Sunday Night at the London Palladium and Dylan’s record didn’t hit the charts until May 1964, but it reached the Beatles much sooner. John Lennon recalled: “We didn’t stop playing it. We all went potty about Dylan.” George Harrison said: “We just played it, just wore it out. The content of the song lyrics and just the attitude – it was incredibly original and wonderful.”

“Robert Allen Zimmerman, as he had once been known, had taken poetry off the bookshelves, paired it with melodies of folk-like simplicity accompanied by guitar and harmonica, and loaded it on to the jukebox.”

The record demonstrates the polarities of Dylan’s songwriting: ‘Girl from the North Country’ is the most tender of his love songs, ‘Masters of War’ the most bitter and angry of his protest songs, with a final verse (wishing death on those same masters of war) so severe that Judy Collins couldn’t bring herself to sing it. ‘Oxford Town’, a song culled from newspaper headlines about James Meredith and the forced integration of the University of Mississippi, is part of the great chronicle of America’s civil rights struggle with which Dylan, under Rotolo’s influence, was then engaged.

Then there’s ‘A Hard Rain’s a-Gonna Fall’. At one stage Dylan claimed the song was written as the Cuban missile crisis unfolded in 1962 (“I thought I wouldn’t have enough time alive to write all those songs, so I put them into this one”) but in fact he first performed ‘A Hard Rain’ at the Sing Out! annual hootenanny at Carnegie Hall on 22 September 1962, exactly a month before the nationwide television address in which President John Kennedy revealed “unmistakable evidence” of Soviet missiles heading for Cuba.

‘Blowin’ in the Wind’, which opens Freewheelin’, is Dylan’s best-known song, sung by people of all ages around the world, many of whom have no real knowledge of its author. Composed in spring 1962 and one of the first songs on the album to be recorded, it has passed into the folk tradition from which its melody was purloined. It was as effective at protests against the Iraq war in 2002-03 as it was at Vietnam demonstrations decades earlier. It’s been sung in classrooms and churches, and Dylan himself sang it for Pope John Paul II at the 1997 World Eucharistic Congress in Bologna. The song’s opening line (“How many roads must a man walk down/ Before you call him a man?”) is “the Ultimate Question” in Douglas Adams’ The Hitchhiker’s Guide to the Galaxy.

Joan Baez and Dylan perform at the 1963 Newport Folk Festival

Following the album’s release, Dylan travelled to California to perform at the Monterey folk festival, where Joan Baez joined him on stage. Peter, Paul and Mary’s cover of ‘Blowin’ in the Wind’ was climbing the charts in the run-up to July’s Newport Folk Festival where, four years earlier, Baez’s unannounced debut had made her an overnight star. Now the planets were aligned for Dylan, who appeared on each of its three days, including the closing night, when Baez brought him on stage for ‘With God on Our Side’.

Freewheelin’ was one of 50 recordings chosen by the Library of Congress in 2002 to be added to the National Recording Registry. Part of the citation read: “This album is considered by some to be the most important collection of original songs issued in the 1960s. It includes ‘Blowin’ in the Wind,’ the era’s popular and powerful protest anthem.”

The Freewheelin’ Bob Dylan marks the beginning of a remarkable three-year period during which Dylan released a series of albums that each broke new ground: The Times They Are a-Changin’, Another Side of Bob Dylan, Bringing It All Back Home, Highway 61 Revisited and Blonde on Blonde.

Dylan and Suze Rotolo in New York in September 1961

Dylan’s last truly great album was Blood on the Tracks (1975). While his genius has been sporadically evident since then on Oh Mercy (1989), Time Out of Mind (1997), Tempest (2012) and (many would say) Rough and Rowdy Ways (2020), the flame has never burned as brightly as it did on those early albums. Diehard fans may defend his every utterance but, on record and in concert, his performances have long left a great deal to be desired. The seemingly endless production line of his artwork, now degraded by the autopen controversy, suggests that, as Dylan wrote in 1965, “money doesn’t talk, it swears”.

Mozart and Gershwin died young, the Beatles disbanded. Bob Dylan – like so many rock stars – plays on into old age, the preservation of dignity increasingly difficult. But 60 years ago, he changed music for good.

Liz Thomson is a journalist, author and the founder of The Village Trip, an annual festival celebrating the history and heritage of Greenwich Village, New York City.

This piece was taken from Anniversary, the 11th edition of Tortoise Quarterly, our short book of long reads. A print copy is available for purchase on the Tortoise shop – members’ get a special discount.

Photographs John Byrne Cooke Estate/Getty Images, Jan Persson/Redferns, Michael Ochs Archives/Getty Images, Brian Shuel/Redferns, Jeff Hochberg/Getty Images