Near the end of his career Hendrix was certainly in the midst of a musical transition, one that, if he had lived, could have taken him outide of his role as a popular hero into the more experimental world of jazz. He certainly discussed this with Miles Davis, with an album muted with legendary jazz arranger Gil Evans.
It never happened, of course, but you dont have to look too far to find jazz musicians with the same flair, the same musicianship and the same capacity to fly their freak flag very high.
I'm not talking about the free jazz crowd, Ornette Coleman, Anthony Braxton; my own personal view is that this was music that made a critical point but really wasnt all that listenable. The freak flag was a bit too high
I'm talking about the half way point between hard-bop and free jazz, 1961 to about 1969 generally. In many ways jazz was ahead of rock during this period in terms of experimentation; and jazz of course was many decades behind classical.
This is Hendrix on sax, Ravi Shankar on piano, Arthur Brown on trumpet, with a solid rhythm section holding it all together.
If you like the sound of that give these a go
1. You've Got to Have Freedom Pharoah Sanders
2. The Stolen Moment Eric Dolpy
3. I Say a Little Prayer Roland Kirk
4. Black Narcissus Joe Henderson
5. Sister Mamie Yusef Lateef
6. Prince of Peace Pharoah Sanders
7. Blue Nile Alice Coltrane
8. Air Cecil Taylor
9. Thelonius Sphere Monk Art Ensemble of Chicago
10. African Song Yusef Lateef