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Experimental hip hop as an avant-garde art movement has many roots from which it evolved. From a grass roots perspective some of the earliest pioneers of hip hop itself planted the seeds from which some of the most widely recognized underground urban artists grew out of.
(In no particular order & by no means are these lists complete)
Pioneers:
-Africa Bambaataa
-Grand Master Flash
-Prince Paul (most notably, his work with De La Soul & his experiments on Wordsound Records)
-Boogie Down Productions
-the Bomb Squad (Hank Shocklee/P.E.)
-Mantronix
Rooted Contemporaries & influences of these Pioneers:
-Art of Noise
-Kraftwerk
-Yellow Magic Orchestra
-Tom Tom Club (Tina Weymouth & Chris Frantz of Talking Heads)
list of "new-skool" experimental hip hop artists:
-Anti-pop Consortium
-Airborn Audio
-Beans
-Tes
-DJ Shadow
-DJ Krush
-Kool Kieth
-RZA
-Spaze Crafte One
-Saphryn Follicle Audio
-No Surrender
-Seraphim (of No Surrender)
-Hangar 18
-El P
-Atomz Family
-Kid Koala
-Ruido Mentol Nomad
-Bill Laswell
-Sensational
-Scotty Hard
-Dose
-Jel
-X-Ecutioners
-Rob Swift
-DJ Qbert
-Birdy Nam Nam
-Machine Drum
-Prefuse 73
-Afra & the Incredible Beatbox Band
-Invisible Scratch Pickles
-DJ Spooky (that subliminal kid
Labels that foster the experimental hip hop genre:
-Soup Disk Recordings
-OM Records (Deeper Concentration Compilations)
-Asphodel
-Wordsound Recordings
-Lex (sub-division of WARP Records)
-Anticon
-ION Records
-Ninja Tunes
-M3rck
-Chocolate Industries