The February, 1966 interview with Bob Dylan was simply put, a portrait of the artist at the top of his game. Before the motorcycle accident, the “Judas” labeling, the noodling around with The Band in an upstate New York basement, and on the verge of putting out what might be his greatest achievement in a career full of high points, Blonde on Blonde, Dylan talked to Playboy.
What caused Bob Dylan – whose disdain for the media has been well-documented – to grant his longest interview at the time with a magazine that is known more for nudity than journalism? Maybe Dylan felt some sort of connection with the magazine’s subversiveness. Or was it the possibility of being questioned by a well-respected writer like Nat Hentoff? Maybe he was just promised a free lifetime subscription.
Read: Bob Dylan interview with Nat Hentoff for Playboy, Feb. 1966