The most common entry point for Grateful Dead listeners is the acoustic folkie material, especially "Uncle John's Band". That makes sense; the song is fun, memorable, and relatively accessible. It seems like it would make a good campfire singalong. But then you get in there to try to learn it, and the song turns out to be extremely odd. Like a lot of Dead tunes!
This excellent episode of the 500 Songs podcast tells how label executive Joe Smith was ecstatic when he heard UJB for the first time. He supposedly ran into the hallway and grabbed people, shouting “We’ve got a single! We’ve got a single!” UJB was the first Dead song that made it onto the Hot One Hundred, getting up to number sixty-nine. It sounds very little like "Touch of Grey", the only Dead song to hit the top ten, but both songs share a kind of wry "what are you gonna do" attitude.
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