There are 38 Dylan songs in the Dead’s live catalog.
I have gravitated to one collaborative recording in particular, “Queen Jane Approximately” from Bob Dylan’s 1965 double album, Blonde on Blonde. I am torn as to which is my favorite live rendition. I first listened to the Dylan cover compilation recording on Postcards of the Hanging (Grateful Dead/Arista). It was recorded on December 29, 1988 at The Oakland Coliseum in California. Bob Weir handles the lead vocal with Dylan inflections on a couple of stanzas.
I next listened to the Dylan & The Dead live recording on Bob Dylan’s Columbia label. This live recording happened first on July 19, 1987 in Eugene, Oregon.
It is amazing that Bob Dylan and The Dead performed live in concert together at all. If you attended in person any of the Dylan and Dead live shows you probably never knew that it was indeed a simple twist of fate that Bob Dylan and The Dead gelled as a performance nucleus.
Read this Open Culture educational media article about the Dead and Dylan rehearsals to learn more about what finally changed Bob Dylan’s mind to agree to the tour. Bob Dylan’s wry wit about the often Dead rumored “acid-trip” is expressed about the shows at the end of his two-level quote. There is also an audio link on that page that lets you play individual tracks from the 74 song five-hour+ rehearsal!
In Chronicles, Volume 1 he writes:
After an hour or so, it became clear to me that the band wanted to rehearse more and different songs than I had been used to doing with Petty. They wanted to run over all the songs, the ones they liked, the seldom seen ones. I found myself in a peculiar position and I could hear the brakes screech. If I had known this to begin with, I might not have taken the dates…. There were so many [songs] that I couldn’t tell which was which-I might even get the words to some mixed up with others.
Dylan eventually excused himself from the studios, intending never to return. But an encounter with a local jazz band — call it a simple twist of fate — brought him back. Dylan and The Dead started playing through his big repertoire. It was tough sledding at first. “But then miraculously,” he adds, ”something internal came unhinged.” “I played these shows with The Dead and never had to think twice about it. Maybe they just dropped something in my drink, I can’t say, but anything they wanted to do was fine with me.”