Ornette Coleman was exactly the kind of musician you’d expect to sit in with the Grateful Dead. As a pioneer of the free jazz movement, Coleman—like the Dead—helped push music into uncharted territory during the 1960s and beyond. Furthermore, Jerry Garcia was a longtime fan of the forward-thinking saxophonist, who himself became a fan of the Dead after witnessing a show at Madison Square Garden in 1987 (Garcia also contributed his chops to three tracks on Coleman’s 1988 album Virgin Beauty).

“I was so overwhelmed by the audience,” Coleman told Rolling Stone in 1989. “They have total dedication. They’re 100-percent Dead fans. They could have done anything up there and those people would have screamed.” The saxophonist added that it was refreshing to see “a successful band playing in a way where whatever they decided to do, that audience wasn’t going to walk out. I thought, ‘Well, we could be friends here.’ Because if these people here could be into this, they could dig what we’re doing.”

Coleman finally got his chance to get in on the magic a few years later when his band Prime Time supported the Grateful Dead during one of the band’s annual Mardi Gras concerts at Oakland-Alameda County Coliseum on February 23, 1993. Prime Time’s two-drummer format and penchant for far-out improvisation made them a top-notch opening act, but it was Coleman’s second set collaboration with the group that stole the show.

In keeping with his avant-garde roots, Coleman made his first appearance during a heady “Drums” > “Space” segment that also featured some interesting work from didgeridoo master Graham Wiggins. That madness was followed by a mesmerizing “The Other One” that went off the rails for a solid six minutes before the song even came into focus, eventually giving away to a truly unique “Stella Blue”. Finally, a set-closing rendition of Bobby Bland‘s “Turn On Your Lovelight” gave Coleman a chance to turn up the heat with some more conventional, though no less refined, playing. Throughout all of it, the free jazz pioneer refused to play it safe or fall into the background, making for a special collaboration worthy of celebrating a quarter-century later.

You can give the full show a listen below, though Coleman doesn’t join the fray until “Drums”:

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[Audio: Jonathan Aizen]