Rolling Stone at 50: Interviewing Bob Dylan

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Delve into the history of Bob Dylan’s deep relationship with Rolling Stone, reflected in nine major interviews dating back to 1969. Michael Ochs Archive/Getty

On June 3rd, 1968, eight months after the first issue of Rolling Stone hit newsstands, editor and publisher Jann Wenner sat down at a typewriter and wrote Bob Dylan a letter. “I don’t mean to add to the number of people that pester you every day,” he wrote. “But we would like very much to include some direct coverage of your activities in our publication. You don’t have to tell us what kind of oatmeal you like in between meals, but it would be nice to let us and our readers know what you think about your music and what is happening in popular music today.”

Wenner, 22, couldn’t
 have imagined he was kicking off a 50-year relationship between Dylan and Rolling Stone, one that would produce one revelatory interview after another. The nine major interviews represent an ongoing 
conversation with the most important songwriter of 
the past century, as well as his primary forum for communicating with fans beyond his songs. (In 2006, they were collected in the book Bob Dylan: The Essential Interviews.)

Dylan’s connection to Rolling Stone predates the first issue. San Francisco Chronicle columnist Ralph Gleason was one of the first critics to recognize the singer’s immense talent. “Genius makes its own rules,” Gleason wrote in 1964. “And Dylan is a genius, a singing conscience and moral referee as well as a preacher.” Three years later, when Gleason and Wenner started a new magazine, they named it largely in honor of Dylan’s “Like a Rolling Stone.”

At the time of Wenner’s letter, Dylan had been out of the public eye for three years, following a motorcycle accident in upstate New York. “Getting Bob to speak would be a big coup,” Wenner says. “And by this point, he’d seen Rolling Stone and had a sense it was a for-real thing and it was in his philosophical wheelhouse, something genuine that would appeal to him.”

It took a few more letters and a couple of near-misses, but by June 1969, Dylan was ready to talk. Over several hours in a Manhattan hotel room, Wenner asked Dylan about everything from his new, sweeter singing voice (“Stop smoking those cigarettes and you’ll be able to sing like Caruso,” Dylan explained) to The Basement Tapes, first revealed to the public in the pages of Rolling Stone in a June 1968 article by Wenner. He also got Dylan to address the subject that was on the world’s mind: why he’d disappeared in recent years. “Well, Jann, I’ll tell ya,” Dylan said. “I was on the road for almost five years. It wore me down. I was on drugs, a lot of things … And I don’t want to live that way anymore.”

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Wenner’s 1968 letter to Dylan requesting an interview.

For his epic two-part interview with Dylan in 1978, Jonathan Cott sat down with the songwriter for marathon sessions that took place all over: backstage at a Portland, Oregon, concert; a tour bus; a hotel; and a restaurant, where Cott and Dylan shared a drunken meal. “Our discussion got a little bit … lively,” Cott recalls.

The interview was timed to the release of Dylan’s film Renaldo and Clara. Cott asked Dylan why he made himself so vulnerable by putting out a movie that starred his ex-wife, Sarah, alongside Joan Baez, another ex. “You must be vulnerable to be sensitive to reality,” Dylan said. “And to me, being vulnerable is just another way of saying that one has nothing more to lose. I don’t have anything but darkness to lose. I’m way beyond that. … It has
 nothing to do with the breakup of my marriage. My marriage is over. I’m divorced. This film is a film.”

The first part of the interview ran as a cover story in January 1978. (It was Dylan’s ninth Rolling Stone cover; there have been 19 in all.) Annie Leibovitz shot the cover during a loose session in her New York studio, capturing an iconic image of Dylan in shades. The second part of the interview ran in November ’78 – with a cover that found Dylan in a less-playful mood. It was shot 
at the end of a long tour, and 
instead of allowing a Rolling Stone photographer in, Dylan had a buddy snap some images in the bathroom of Madison Square
 Garden. (A urinal is clearly visible on the cover.)

~~~  READ THE INTERVIEW  ~~~

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