In 1879, Japan annexed the Ryūkyū Islands, dissolving the nominally independent Ryūkyū Kingdom and establishing Okinawa Prefecture. This helped inaugurate Imperial Japan’sexpansion beyond the historical naichi or “inner lands.” It also set in motion a structural transformation of Okinawan society, marked by the end of tribute trade with China, the abolitionof a centuries-old status system, and the gradual modernization of the economy. This process was painful, pitting the interests of the traditional Okinawan elite against those of Japanese administrators, with Okinawan peasants and laborers caught in the middle. The epicenter of this process was the prefectural capital of Naha – and for many Okinawans, particularly working class women, the soul of Naha was its commercial theater. This dissertation approaches prewar Okinawan commercial theater both as an institution and as a space of experience and expression. Its main focus is vernacular musical drama or kageki, which was created by classical performing artists disenfranchised by the dissolution of the court. Musical dramas such as A Peony of the Deep Mountains (Okuyama no botan) and Iejima Romance (Iejima Handō-gwa) draw selectively on both courtly and popular traditions, fusing the poetic sophistication of kumiodori dance-drama with the mass appeal of folk song and dance. After introducing early modern courtly and popular performing arts, I trace the emergence of commercial theater as an effect of contradictory social forces set in motion by annexation. Cross-reading actors’ memoirs and newspaper reviews with writings by period scholars such as Okinawan cultural historian Iha Fuyū and Japanese critical theorist Tosaka Jun, I situate commercial performance in its socioeconomic and ideological context. I then turn from a social scientific to a hermeneutic mode of critique, offering close readings of four influential musical dramas. Unlike coeval Okinawan elite literature, these dramas do not explicitly challenge the dominant order. I will argue, however, that by representing low-status female protagonists as self-constant and morally competent agents, they invite working class female spectators to reimagine the horizons of their social experience.