The fundamental issue with the Wilentz book is that it’s a decade old. Things have changed, to say the least.
The Aaron Copland / Bob Dylan connection
Do I have your attention now?!
I am about 2/5th's the way into an amazing book that anyone with the slightest interest in American art forms should find well worth his or her time. It was written by Sean Wilentz, a Professor of American History at Princeton, and author of a few books on that subject. But the book I'm reading is entitled Bob Dylan In America, and it is, hands down, the best writing on Dylan I have yet to read. And I have read a lot about Dylan!
Wilentz starts the book by laying out the context within which Dylan's work will be examined and discussed, starting with the very American music of Aaron Copland. I guarantee you, you have never before heard what Wilentz has to say about the connection between that composer and Dylan. The next section is about the overlap between the Beat writers and the Folk singers of the late 50's and early 60's, but not without tracing their origins back to the 1930's. The relationship between Dylan and Allen Ginsberg is discussed in great detail, and continues into future chapters. It is fascinating stuff.
Wilentz finally gets to Dylan himself, and provides details on the writing and recording of Bob's first six albums, as well as the live shows coinciding with them, culminating in by far the best examination of his masterpiece, "Blonde On Blonde", I have read. Every song, every recording session, every musician involved (there are some surprises!), all examined with fanatical attention to detail. I thought I already knew a lot about the album, but I learned much more than I already knew. Absolutely fantastic!
I do believe this may be the best book I have ever read on the subject of, not just Dylan, but of any artist. I found it at my Public Library, but I'm going to buy a copy. That I'll want to read it again I have no doubt.