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After the release of Electric Ladyland (1968), the final album Jimi Hendrix recorded with his Experience, Hendrix spent the last two years of his life experimenting with different lineups and various musical styles. He even planned a studio date with Miles Davis. (It never happened.) But the only album he released was a live LP made with Billy Cox and Buddy Miles.

That trio, called the Band of Gypsys (Cox on bass, Miles on drums and vocals), played the Fillmore East at the close of ’69. Recordings from that night were edited and released as Band of Gypsys (1970), an album Hendrix didn’t love but nonetheless featured several strong tracks (see: “Machine Gun”).

Yet the Band of Gypsys didn’t last long into the new decade. Before long, Hendrix went back to using Mitch Mitchell as his primary drummer. That closed a brief but fascinating chapter in Hendrix’s career. For Miles, his recording run with Hendrix actually began during the Electric Ladyland sessions.

Buddy Miles’ 1st Jimi Hendrix recording was ‘Rainy Day, Dream Away’

Buddy Miles smiles as he plays drums in 1999
Buddy Miles performing on stage in 1999 | John Atashian/Getty Images

To say Buddy Miles got started in the music business would be a grand understatement. The Omaha-born performer met Hendrix earlier in the ’60s, while Miles (then 16) was playing for Ruby and The Romantics. Hendrix, then with the Isley Brothers’ band, didn’t forget him.

Miles and Hendrix crossed paths again at the Monterey Pop Festival in June ’67. By that point, Hendrix had launched his Experience; Miles was playing with the Electric Flag. A year later, Hendrix had become an international star, and Miles would turn up at New York’s Record Plant to jam with him.

During that period, Hendrix was late in the sessions that would provide the recordings for Electric Ladyland. And though Hendrix loved Mitchell’s work on drums, he always liked to try new combos. One day, he decided to work with a group that recalled a Jimmy Smith quintet.

“We’re gonna do a slow shuffle in D,” organist Mike Finnigan recalled Hendrix telling him in Hendrix: Setting the Record Straight (John McDermott, 1992). “You be like Jimmy Smith and I’ll be Kenny Burrell.” With Miles on drums and few other players aboard, the group jammed on what became “Rainy Day, Dream Away” and “Still Raining, Still Dreaming.”

Miles also recorded with the Experience pre-Band of Gypsys

Jimi Hendrix performing at an outdoor festival in 1969
Jimi Hendrix performs onstage at the Newport Pop Festival on June 20, 1969. | Vince Melamed/Michael Ochs Archives/Getty Images

By the close of Electric Ladyland sessions, the Experience’s run as a three-piece unit was winding down. In October ’68, with the album already in stores, Hendrix tried something different after a recording session with Redding and Mitchell didn’t bear any fruit.

A few days later, Hendrix added both Miles and Lee Michaels (on organ) to his group in the studio. That created the awkward setup of both Miles and Mitchell on drums. But the band made it work and produced “Electric Church — Red House” at the session.

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Early in ’69, Hendrix kept hanging out with Miles, and even produced tracks for the drummer’s new band (The Buddy Miles Express). Meanwhile, Hendrix kept fulfilling tour dates that had been booked for the Experience.

By the summer of ’69, with Redding unwilling to continue with Experience performances, Hendrix began working with Cox on bass and Miles as their drummer. The Band of Gypsys was getting itself together.