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A snapshot of youth. A very special youth, in a very special era, in a very special city. It’s 1963 in New York. Two young lovers walk down an icy street at dusk, huddled against one another. The emotional intimacy of this image would become etched into the minds of millions as the cover art for a ground-breaking album. That album was The Freewheelin’ Bob Dylan, the landmark LP from America’s greatest living singer-songwriter.
The Freewheelin’ Bob Dylan hit record shops on 27 May 1963. Dylan’s second album but first to feature mostly his own songs (his debut was mainly folk standards), the record earnt him the moniker “voice of a generation”. A label that didn’t go down well with Dylan. Freewheelin’ is a powerful record that, while rooted in the folk tradition, also speaks to the very contemporary changes, hopes and anxieties that Dylan is living through. It contains some of Dylan’s most famous songs: the anti-war Blowin’ in the Wind, Masters of War that rails against the arms industry, the dark and complex A Hard Rain’s A-Gonna Fall, the catchy Don’t Think Twice, It’s All Right dedicated to Suze Rotolo, and the mysterious Girl from the North Country. All of them give the world a first glimpse of Dylan’s talent for compelling songwriting and arranging.
The story behind the cover photo for The Freewheelin’ Bob Dylan
When telling the story of the cover photo for The Freewheelin’ Bob Dylan, we have to start with the person who took it. The man behind the lens was Columbia Records photographer Don Hunstein, who collaborated with a litany of legendary musicians in the sixties. Notable work includes cover photography for jazz greats John Coltrane and Thelonious Monk. Hunstein also shot the cover photo for Dylan’s debut album under the guidance of art director John Berg.
The location is Jones Street in New York’s vibrant Greenwich Village. At the time, the neighbourhood was the epicentre of the artistic, political and cultural revolution bubbling away in the Big Apple. It was here, on the corner with West 4th Street, that Dylan rented a flat together with Suze Rotolo – his then girlfriend and the other person pictured on the cover. Initially, a shoot was set up in their apartment. But after snapping a couple of unsatisfactory shots inside, Hunstein suggested the couple take a walk outside. And that’s where he captured the immortal pose, Dylan hands in trouser pockets, Rotolo clinging to his arm.
It was freezing, as you can tell from Dylan’s grimace and the snow lining the street – the shoot took place on a February afternoon. Rotolo recalled that she had to put on extra layers (including one of Dylan’s jumpers) beneath her green coat, which, she said, made her look like a “sausage”. Dylan, however, put his appearance first: he’s clearly shivering in just his leather jacket!
Suze Rotolo: the (accidental) cover co-star on The Freewheelin’ Bob Dylan
There’s something fresh and new about the cover for Freewheelin’. That’s why it made such an impression. The image has a spontaneity and intimacy hitherto unseen in album photography.
As Rotolo explained, in those days most album covers featured contrived and posed photos. But this one is totally different. Hunstein believes it turned out so well because Rotolo put Dylan at ease. Funnily enough, her appearance was down to happenstance: she was not meant to feature on the cover originally.
Yet Rotolo was a key figure, not just for the record cover, but for Dylan himself at the time. The daughter of Italian communist immigrants, she was very politically active and got Dylan – a 20-year-old Minnesotan newly arrived in New York – involved in the civil rights movement. It was Rotolo whom Dylan would get to read his songs. And it was to Rotolo whom Dylan would send heartfelt letters of love and loneliness during her long trip to Italy in 1962. The pair split in the summer of 1963, but Dylan still carried a torch for her years later.
The many imitations of The Freewheelin’ Bob Dylan cover
The choice of that particular photo from the many shots Hunstein hurriedly took as the sun went down that afternoon in 1963 seems to have been Bob Dylan’s. Perhaps because the pose reminded him of a famous photo of his idol, the actor James Dean, taken in 1954 by Dennis Stock in Times Square.
The Freewheelin’ cover has been much imitated and quoted since its release. A few years back, Dylan’s pose even became a TikTok trend, while countless comics have tipped their hat to the cover over the years. Levi’s even brought out an exact replica of the jeans Dylan is wearing in the picture.
Then there’s cinema. In one scene in his 2001 film Vanilla Sky, director Cameron Crowe recreated the same image in painstaking detail, but swapped out Bob Dylan and Suze Rotolo for Tom Cruise and Penelope Cruz.
Another film that owes a debt to Freewheelin’ is Inside Llewyn Davis, the Coen brothers’ movie that follows a week in the life of a young folk musician in Greenwich Village in 1961. The film takes its colour palette from the album cover, which it also references on the official poster.
Staying with the big screen, two films about Dylan – Todd Haynes’ I’m Not There (2007) and James Mangold’s A complete Unknown (2024) – explore the singer-songwriter’s life at the time that the iconic photo was taken.
Over 60 years on, the cover for The Freewheelin’ Bob Dylan has lost none of its power to evoke young love – and a seminal era in popular culture.
Are you fond of The Freewheelin’ Bob Dylan’s cover? Does it make you sigh and smile? Has it inspired any of your creations?