The article explores the unique friendship and creative synergy between two towering figures of late Soviet underground culture, the avant-garde jazz musician Sergei Kuriokhin and the poet Arkady Dragomoshchenko. Both outsiders in Leningrad, they shaped its literary and musical landscapes without aligning with any movements. Dragomoshchenko, a seminal poet, defied categorization, while Kuriokhin, a polymath, challenged conventions across music, performance, and politics. Their collaboration epitomized innovation, blending Dragomoshchenko’s cerebral poetry with Kuriokhin’s avant-garde music. Despite linguistic barriers, their connection transcended verbal communication, rooted in shared modes of nonlinear thinking and creative experimentation. Kuriokhin’s revolutionary Pop Mekhanika, a chaotic fusion of genres and sensory experiences, mirrored Dragomoshchenko’s relentless poetic evolution. Their friendship catalyzed pivotal encounters, such as with the American poet Lyn Hejinian, expanding their artistic horizons. Dragomoshchenko’s poetic vision, centred on perception’s fleeting nature and the boundaries of possibility, echoed Kuriokhin’s multisensory assaults on audience expectations. Through their unconventional artistry, Kuriokhin and Dragomoshchenko navigated the shifting cultural landscape of late Soviet society, embodying a spirit of defiance and exploration. Their enduring influence transcends their untimely deaths, leaving an indelible mark on Russian avant-garde culture.