In the two decades between the first staging of Gluck’s Orfeo in 1903 and the end of Asakusa Opera in the great fire of 1923, musical theatre in Japan saw a rapid process of adoption and transformation. But despite the well-known role of Italian choreographer Giovanni Vittorio Rosi in the training and performance of Western opera at the Imperial Theatre in Tokyo, the association between opera and Italy that was so prominent in other parts of the world never quite took hold. The chapter interrogates the limits of the appeal of italianitá in the history of transnational operatic encounters. These limits are in part rooted in the general difficulties of transplanting a composite cultural form to a foreign setting and its hybridisation with local cultural practices. The chapter discusses the nation-building goals of the Meiji government and the translation of librettos, the Wagnerian moment among Japanese artists and intellectuals and the general conditions of cultural exchange in Meiji Japan and their effects on perceptions of Italianness.