Garcia spoke of the song in an interview;
Hunter and I always had this thing where we liked to muddy the folk tradition by adding our own versions of songs to the tradition .... We had our Casey Jones song. We had our Stagger Lee song. Dupree's Diamond Blues is another one of those. It's the thing of taking a well-founded tradition and putting in something that's totally looped. So that's Hunter's version of that. Originally it's one of those cautionary tales; one of those 'Don't take your gun to town' type tunes. So Hunter elaborated on that in a playful way.Garcia also spoke about Dupree's in an interview for Rolling Stone in 1971;
It reminds me of a little cartoon strip, with cartoon characters. It has a banjo in it, a little 12-string and stuff like that. Texturally it's really successful to my ears. It does what it's supposed to do.Dupree's Diamond Blues made sporadic appearances in the live repertoire over the years. It was performed regularly between January and July in 1969. It then disappeared until half a dozen or so performances in late 1977 and early 1978. It's next revival was in August 1982 after which it was played fairly regularly until the Fall of 1988. After this there were just three solitary appearances in 1989, 1990 and 1994.
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