@jafant: I find the post-’66 period very interesting myself. While in 1967 the Rock world was turning to psychedelia, long instrumental jams, and non-U.S.A. instruments and music forms (I consider the introduction of the sitar into Rock ’n’ Roll a miserable idea. Does anyone actually like "Within You Without You"? Oy!), Dylan spent the whole year in the basement of Big Pink, schooling The Hawks in all things American), recording the musical collaboration that became known as The Basement Tapes. That year has already been covered in the great Bootleg Series Vol. 11 that Columbia finally put out in 2014.
Then on December 27th of 1967, out of nowhere Dylan reappears with the very low key John Wesley Harding album, which could not have been more different from what everyone else was doing (and what Dylan had himself doing on his last album, Blonde On Blonde) if Dylan had tried. Actually, that is perhaps exactly what he was doing with that album. I remember hearing it and being completely mystified. I was in the throes of my Cream/Hendrix/etc.phase, which I didn’t snap out of until the Summer of ’69.
I heard Music From Big Pink when it was released in June of ’68, but found it incomprehensible. It wasn’t until that Summer of ’69 that I had my musical epiphany, so when The Band’s "brown" album came out that year I was ready for it. I also found a copy of the 2-LP bootleg of The basement tapes, and set about studying them. Every other musician I knew (well, the good ones at least) was doing the same.