The cover of the 1963 album "The Freewheelin' Bob Dylan" shows Dylan moving through the snowy streets of Greenwich Village with a young woman at his side. It is she, rather than Bob who looks straight into the camera, and therefore straight at the viewer, and therefore, straight at the teenager I was at the time I bought the record (about 15 years after its release). To my mind at the time, she seemed to affirm our mutual enthusiasm for Dylan (albeit perhaps for different reasons), and this made me feel a sort of distant connection with her. The young woman is Suze (pronounced "Suzy") Rotolo, 19 years old and Dylan's girlfriend at the time. Rotolo died last month at age 67, not long after publishing "A Freewheelin' Time," her memoir of the years so iconically captured by that photograph. She certainly deserved to be on the cover of Dylan's albums. It had been Rotolo who had introduced Dylan to the poet Rimbaud and to the songs of Brecht and Weill, both of which Dylan considered important influences. However, having a relationship with a man like Dylan couldn't have been easy at the best of times; to try to ride the out-of-control bronco that was Dylan's rocketing career at the time must have seemed impossible.
Indeed, it wasn't long after "The Freewheelin' Bob Dylan" was released that Dylan and Rotolo broke up. In a way, the writing had already been scrawled on the wall before the cover photo was even taken. In the previous year, 1962, Rotolo had gone with her mother to Italy. It was clear that her family wanted her to put some space between Dylan and herself, and the tactic seemed to work when Suze decided to stay on, turning the scheduled short vacation into a six-month stay. Dylan felt the relationship was over, and he wrote one of his most moving songs, "Boots of Spanish Leather" (Spain standing in for Italy) to capture the sense of desolation he felt. As it happened, Rotolo did eventually come back; she and Dylan were re-united; according to her memoirs, Rotolo became pregnant but then had an abortion; then she and Dylan broke up permanently. At this point Dylan became quite deeply bitter and in that frame of mind, he wrote the scathing song "Ballad in Plain D" describing in the most thinly veiled terms how, in his view, Rotolo's family had poisoned their relationship. Dylan later regretted having written and recorded that song, and he never performs it anymore. However, the song "Boots of Spanish Leather" he does perform, and it remains an honest and thoughtful rendering of the growing sense of hopelessness that attends the apparent end of a relationship. Interestingly, Dylan never allowed any other private relationship to be photographed as frequently as he had permitted himself to be shot with Rotolo, and that fact helps to create an extra aura of precious innocence around this youthful relationship. For after this time, Dylan guarded his private life much more jealously, and so in most of his off-stage photographs, we see him alone, isolated, free from attachments: an existentially absolutely self-determined figure.
Here's a short film I put together using a 1999 bootleg recording of Dylan performing "Boots of Spanish Leather."
