The discourse surrounding psychedelics is problematic on several vectors. The investigation of their effects on human beings is illegal in most circumstances, yet exploration continued after their scheduling in the late 1960s and early ’70s. The article examines this problematic from the viewpoints of four leading psychedelic outlaws—Terence McKenna, Philip K. Dick, Timothy Leary, and John Lilly—who continued their explorations and wrote extensively about these experiences post-illegalization. The paradox of prolixity in the face of unspeakable or ineffable experience is one dimension of the problematic. The author weaves in her own experiences of encounters with a language from the psychedelic sphere, in light of the call for new language to communicate about and with the spheres of experience contacted through psychedelic self-exploration.