Dylan expert and longtime Rolling Stone contributor Jonathan Cott has compiled thirty-one interviews that, taken together, present the public transformation of a brilliant young man evading fame and its attendant invasion of privacy into a seasoned professional who has learned how to impart truth to those questioning him without giving away too much of his private self.

Included in Bob Dylan: The Essential Interviews are all six major interviews Rolling Stone conducted with Dylan, by Jann S. Wenner, Mikal Gilmore, Kurt Loder, and Cott himself. Other highlights include Nat Hentoff's legendary 1966 Playboy interview with the singer; Studs Terkel's 1963 radio interview on Chicago's WFMT; the interview Dylan gave to screenwriter Jay Cocks when Cocks was a Kenyon College student in 1964; a 1965 interview with director Nora Ephron; and an interview that Sam Shepard turned into a one-act play for Esquire in 1987. Each piece portrays Bob Dylan as an interview subject who, as Cott writes in his introduction, is "at once obviously reluctant, self-protecting, and self-concealing but equally often a stunningly direct, heartfelt, epiphanic, poetic, and, most important, playful expositor of his munificent and inspiring thought-dreams."