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."
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.)
When Kurt Loder sat down with Dylan in 1984, his songwriting was at a very different place: Dylan's born-again Christian phase had come to an end, and he was trying to find his place in the MTV age. Dylan was in an especially combative mood, giving sharp responses on everything from his religious conversion ("I've never said I'm born-again, that's just a media term") to his anti-NASA lyrics ("What's the purpose of going to the moon?"). "All you can do is sort of report what he says," Loder says today. "You can't parse and say, 'You know, well, but this isn't true.' 'Cause it may be true to him in some way or another."
But even as he sparred with the magazine's interviewers, Dylan maintained a friendly relationship with Wenner. When Dylan came to town over the years, Wenner would often visit him backstage. In November 1999, Dylan even called out to him from onstage, something he rarely does to anybody in the audience. "There's a lot of people from Rolling Stone here tonight," he said. "After the show, they're gonna come backstage and interview me, then I'm gonna interview them."
In 2007, Wenner caught up with Dylan in Amsterdam for an interview tied to Rolling Stone's 40th anniversary. He found himself literally begging Dylan to take their conversation seriously. "You're not being very helpful with this," Wenner said. "What can I do to get you to take this seriously?" Dylan flipped it around on him. "I'm taking it seriously," he said. "Of course I am. You're the one who's here to be celebrated. Forty years … 40 years with a magazine that obviously now has intellectual recognition." Wenner ran the back-and-forth verbatim. "People loved that part," says Wenner. "I'm just there being the reader. I'm just working on your behalf to put you in that room with this person."
They eventually got into a conversation about the themes on Dylan's new album Modern Times, which expresses a dark, almost terminal view of America. "We really don't know much about the great Judgment Day that's coming," Dylan said, "because we've got nobody to come back and tell us about it. We can only assume certain things because of what we've been taught. ... I think as we get older, we all come to that feeling, one way or another. We've seen enough happening to know that things are a certain way, and even if they're changed, they're still going to be that certain way."
For the magazine's next interview, in 2009, Wenner called on renowned historian Douglas Brinkley, who traveled to Paris. He found himself backstage watching Dylan shake hands with French President Nicolas Sarkozy and his wife, Carla Bruni. "I can see why he's the head of France," said Dylan. "He's genuine and warm and extremely likable. I asked Sarkozy, 'Do you think the whole global thing is over?' I knew they just had a big G-20 meeting and they maybe were discussing that. I didn't think he'd tell me, but I asked him anyway." Brinkley asked Dylan why he spent decades on his so-called Never Ending Tour. "You never heard about Oral Roberts and Billy Graham being on some Never Ending Preacher Tour," Dylan said. "Does anybody ever call Henry Ford a Never Ending Car Builder? ... What about Donald Trump? Does anybody say he has a Never Ending Quest to build buildings?"
Dylan last spoke to Rolling Stone in 2012, around the release of his Tempest album. When Mikal Gilmore met up with Dylan in Santa Monica, he was greeted by an odd surprise. "He wore kind of a stocking cap, and he had on this red-hair-colored Beatles wig under the cap," Gilmore remembers. "I never asked about it, but it was clearly not his hair. It amused me and sort of threw me from the start."
Gilmore asked about Dylan's tendency to sprinkle recent songs with unattributed quotes from writers like Confederate poet Henry Timrod. It hit a sore point with Dylan. "All those evil motherfuckers can rot in hell," he said, referring to people critical of his process. "I'm working within my art form. It's that simple. I work within the rules and limitations of it. There are authoritarian figures that can explain that kind of art form better to you than I can. It's called songwriting. It has to do with melody and rhythm, and then after that, anything goes. You make everything yours. We all do it."
Every writer who interviewed Dylan got wildly different things out of him, which was precisely Wenner's aim. "Everybody wants to bring something out of him that's pertinent to their point of view about the guy," he says. "And their points of view are as diverse as Bob himself."