I don’t think that interviewing Bob Dylan in 1969 was any more fun that it was when he was tormenting his interviewers in 1965. Jann Wenner, founder of Rolling Stone, scored the coveted “major interview with the reclusive Bob Dylan” as the cover feature of the second anniversary issue of his magazine in November 1969, and it is just a horrible read.

The best part of the interview comes near the end:

WENNER: That’s the awkwardness of this interview.

DYLAN: Well, I don’t find anything awkward about it. I think it’s going real great.

Does he? Does he really think that it’s going great?

At this point Dylan’s relationship with his manager, Albert Grossman, was disintegrating, and he was contemplating leaving Columbia Records (which he would do), although he doesn’t really want to talk to Wenner about either of those things. Wenner asks him about touring and he suggests that he’ll go on the road shortly, but it would be another four years before Dylan would tour again (he did play Isle of Wight between the time this interview was recorded and when it was published). So he lies about the one topic, and just dissembles about the others. This is going great?

One of the most interesting things is that Wenner, who comes across as the nerdiest of nerds here, wants to talk about the specifics of Dylan’s work and Dylan sometimes can’t even remember what songs are on what albums. Either he just didn’t care about this interview (likely) or he has a very unusual relationship to his creativity (possible).

One of the best answers for why he was taking so many drugs while touring in 1965 and 1966:

“My songs were long, long songs. But that’s why I had to start dealing with a lot of different methods of keeping myself awake, alert… because I had to remember all the words to those songs.” If you consider how short most of the songs on John Wesley Harding and Nashville Skyline are, I’m sort of tempted to believe that this might actually be a genuine answer.

The interview does have Dylan explaining that the change in his voice, which is at its most notable on Nashville Skyline, was a result of his decision to stop smoking. This could also be true (apparently Dylan still smokes to this day, and when he tours he often has to stay in low end hotels because they allow smoking). His comment, “I tell you, you stop smoking those cigarettes … and you’ll be able to sing like Caruso.” is probably the high point of the interview.

A lot of the rest of it is Wenner asking Dylan his opinion on other bands of the period, which was probably of interest to the editor of a music magazine (and maybe the readers) but not so much to me. It is interesting when Dylan notes that he doesn’t really know the music of The Grateful Dead, given that they will later tour and record together. This interview does paint a picture of a man who is pretty cut off from the scene he helped generate though.

My take away from all this was that in 1969 Wenner seemed to know a lot more about Dylan than Dylan knew about Dylan, or at least about the public part of his life. Clearly, people spend more time thinking about Dylan than Dylan does. I guess that now includes me.