It must have seemed like a ludicrous double feature on paper: psychedelic rock titans the Grateful Dead playing a show with jazz icon Miles Davis. While the Dead took a jazz-friendly approach to rock and Davis leaned into the headier music styles of the 1960s and 1970s, the two artists seemed to have little else in common. But crucially, Davis was one of the inspirations who helped push the Dead further into the realms of jamming and improvisation, with Garica being an especially keen fan.
“I got part of that from Miles, especially the silences. The holes,” Garcia told Grateful Dead publicist Dennis McNally. “Nobody plays better holes than Miles, from a musician’s point of view. In Indian music, they have what you call ‘the unstruck’, which is the note you don’t play. That has as much value as the stuff you do play.”
So when promotor Bill Graham proposed a double bill featuring the Dead and the Miles Davis Quintet, it was an immediate yes from the Dead camp. Davis needed a little more convincing, but once he met up with the band, he found common ground between their respective approaches to music.
“So it was through Bill [Graham] that I met the Grateful Dead,” Davis wrote in his 1989 autobiography. “Jerry Garcia, their guitar player, and I hit it off great, talking about music — what they liked and what I liked — and I think we all learned something, grew some. Jerry Garcia loved jazz, and I found out that he loved my music and had been listening to it for a long time. He loved other jazz musicians, too, like Ornette Coleman and Bill Evans”.
That’s how, across three nights in April of 1970, Davis opened for the Dead at the Fillmore Auditorium in San Francisco. Davis was unsure how the Deadhead crowd was going to react to his music or whether they would even notice at all. But to his surprise, Davis found a surprisingly attentive audience who were as into the music as he was.
“The place was packed with these real spacey, high, white people, and where we first started playing, people were walking around and talking. But after a while, they all got quiet and really into the music,” Davis wrote. “I played a little something like [from] Sketches of Spain and then went into the Bitches Brew shit, and that really blew them out. After that concert, every time I would play out there in San Francisco, a lot of young white people showed up at the gigs.”
“Looking back, I think Bill Graham did some important things for music with those concerts, opened everything up so that a lot of different people heard a lot of different kinds of music that they wouldn’t normally have heard,” Davis concluded.
The Grateful Dead were noted fans, with Garcia, bassist Phil Lesh, and guitarist Bob Weir eager to take lessons from Davis’ playing. Whenever they could, the Dead would attempt to channel the improvisational approach that Davis had in his music. Although the Dead themselves never directly covered Davis, a number of Garcia’s projects did.
‘So What?’ and ‘Milestones’ both floated in and out of the repertoire that Garcia established with mandolin player David Grisman. Dead & Company even busted out a few takes of ‘Milestones’ throughout their live career. But Garcia only took on Davis’ iconic Kind of Blue track ‘All Blues’ once: with frequent collaborator Merl Saunders during a duo gig that the pair played on June 4th, 1974.
Check out Garcia and Saunders playing ‘All Blues’ down below.