The iconic magazine cover that compared Bob Dylan to Fidel Castro
In September 1965, American men’s lifestyle magazine Esquire dropped one of its most famous covers. Purporting to illustrate who the leading heroes of the nation’s college students were as the country wavered on its cultural pivot, a composite of four different sections of four faces of perceived rebellion was drawn to demonstrate the poster boys vastly different from the War Generation or even the previous decade.
Bottom right was half of assassinated President John F Kennedy’s winning smile, the left side Cuban revolutionary Fidel Castro, and occupying the right eye was militant Civil Rights activist Malcolm X. Deemed to hold the same insurrectionary command was folk troubadour Bob Dylan, his curly Blonde on Blonde hair forming the top left of Esquire‘s artful front collage.
“The Face of a Hero” is a curious assemblage. JFK was very much engaged in the Cold War machinations and imperial interventions as any other US president of the day, greenlighting the embarrassing Bay of Pigs disaster and his administration pushing the CIA to organise Castro’s murder, but his youthful demeanour struck a chord with a student electoral base left cold by Richard Nixon’s first presidential bid.
Castro and Malcolm X—later el-Hajj Malik el-Shabazz after his conversion to Sunni Islam—fit the brief of ‘rebel’ without question, respectively overthrew the hated Batista regime and established the socialist state that exists to this day and challenged the pleas for non-violence popularly preached among the mainstream voices of 1960s Black struggle.
There’s perhaps a slight tongue-in-cheek with Eqsuire‘s political Frankenstein’s monster. Yet to anticipate just how heady and turbulent youth culture would become, the magazine also listed other “college rebels” who had their grip on students at the time. It’s a disparately chequered list. The Berkeley Free Speech Movement’s Mario Savio and New Journalism pioneer Terry Southern stand next to the Vietcong and Spider-Man as every young radical’s inspiration. Easily envisioned as a certain Peter Blake collage that would dominate the rock and pop landscape two years later, Esquire‘s pick of 28 college rebels veers across the spectrum of legitimate political titans to questionable reaches in the day’s pop culture or frivolous gestures of support antagonistic to the US war machine.
While the counterculture was bubbling away, the ‘Summer of Love’ still had not reached its lysergic plume, and even The Byrds hadn’t released their ‘Turn! Turn! Turn!‘ seasonal shift pop smash. Music was still in the aftermath of the British invasion’s infancy, The Rolling Stones’ ‘(I Can’t Get No) Satisfaction’ was only out a month, and with The Beatles’ last LP being Help!, their pivotal songwriting maturation was just out of reach.
Thus, it was Dylan who was leading the fore and music with a social conscience, hailing from the folk revival tradition that scored New York’s Greenwich Village years earlier and then ‘going electric’, gifting the world of roots rock with his polemic and poetic songcraft.
Music and youth culture would take wild detours and leaps forward with each year of the 1960s’ dramatic unfold, but, for a moment, Dylan’s commanding anthems and articulation of the new generation’s values and attitudes saw the original troubadour as a clear agent of disruption of an establishment that had no clue as to what counterculture was materialising.
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