This article centres on the work of Vasily Kalafati (1869–1942), a prominent musical figure of the Greek diaspora in Russia. I examine how Kalafati’s Gypsy Song (Tsyganskaya Pesnya), opus 19 (1927) responds to Soviet nationality politics and inclusive cultural policies, with reference to its engagement with Russian musical Orientalism. Through the lens of the composer’s own lived experience of Otherness as a “small black-faced Greek” in Russia, I identify a fusion of Oriental musical signifiers and Western harmony and conventional tonality in Gypsy Song, suggesting that this functions to destabilize the binary opposition between Self and Other. In these terms, I consider Gypsy Song alongside the composer’s subsequent study, transcription, harmonization, and utilization of folk songs and themes, in the context of Roma people’s efforts to self-Sovietize in the 1920s and 1930s and the musical nation-building projects which were to become central in the Soviet Union in this period.