Credit: Bent Rej

Remembering Bob Dylan’s mystifying and mystical 1965 Playboy interview

In 1965, Bob Dylan had transcended his folk roots and become an icon of the counterculture movement that was swelling with willing participants across the globe. Sick of the ‘old way’ of doing things, Dylan’s poetic mind and free spirit offered swathes of youthful brains an icon to adore.

Dylan’s lyrics in the early 1960s had laid a path of folkloric obscurity for the singer but in 1965 everything changed with one simple plug. Taking the stage at the Newport Folk Festival in 1965, Dylan would betray (in many’s eyes) the folk music world and go electric, prompting cries of “Judas!” from the audience. But it was what Dylan did next that we re-route this star’s journey. Met with boos and hissing, Dylan told his band to “turn it up.”

While 1963’s LP Freehweelin’ Bob Dylan had cemented Dylan as a notable artist, it was this act of musical disobedience that made the singer a household name. No longer resigned to the bookshops and coffee houses of New York’s Greenwich Village or the folk festivals across Europe, the singer had become famous.

It meant that he was a hot commodity for the press and countless interviews ensued and haven’t ever really ended from then on—but there’s one interview which ranks far above the rest. Not for its laser-pointed insight or its revelations of the real Bob Dylan, but because it is both a mystifying and mystical conversation that sees Dylan tackle everything and nothing at all.

The interview was conducted by former Village Voice music critic Nat Hentoff for Playboy and sees Dylan in a captivating mood. First published in 1966, the conversation ranges from rambling to revolutionary and encapsulates everything Dylan was at the time. But while the print version of the interview had some scratching their heads, the full audio is a certified Mensa puzzle for all who listen.

For example, when presented with the question “why rock ‘n’ roll has become such an international phenomenon?” Dylan, with consideration and free-thought, answers: “I can’t really think that there is any rock ‘n’ roll. Actually, when you think about it, anything that has no real existence is bound to become an international phenomenon.” It is this role of philosophical troubadour that Dylan, especially in 1965, played so well.

Yet this answer ranks as some of the most directly intelligible as the singer is deliberately obtuse. Across a range of subjects, he is engaged and intelligent but never attached to any singular answer. It was a facade that the singer would use for years to come.

The truth is, though, this may be one of the most singularly bizarre interviews we’ve ever heard conducted. An interview which delved into the inner-workings of one’s mind, that debated the actuality of rock and roll, and that was both illuminating and confounding—it was just another interview for Bob Dylan.

Listen to the full tape of Nat Hentoff’s Playboy interview with Bob Dylan in 1965.

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