This work examines the creation of an East Asian cultural sphere by the Japanese imperial project in the first half of the twentieth century. It seeks to re-read the “Greater East Asian Co-prosperity Sphere” not as a mere political and ideological concept but as the potential site of a vibrant and productive space that accommodated transcultural interaction and transformation. By reorienting the focus of (post)colonial studies from the macro-narrative of political economy, military institutions, and socio-political dynamics, it uncovers a cultural and personal understanding of life within the Japanese imperial enterprise. To engage with empire on a personal level, one must ask: What made ordinary citizens participate in the colonial enterprise? What was the lure of empire? How did individuals not directly invested in the enterprise become engaged with the idea? Explanations offered heretofore emphasize the potency of the institutional or ideological apparatus. Faye Kleeman asserts, however, that desire and pleasure may be better barometers for measuring popular sentiment in the empire—what Raymond Williams refers to as the “structure of feeling” that accompanied modern Japan’s expansionism. This particular historical moment disseminated common cultural perceptions and values (whether voluntarily accepted or forcibly inculcated). Mediated by a shared aspiration for modernity, a connectedness fostered by new media, and a mobility that encouraged travel within the empire, an East Asian contact zone was shared by a generation and served as the proto-environment that presaged the cultural and media convergences currently taking place in twenty-first-century Northeast Asia. The negative impact of Japanese imperialism on both nations and societies has been amply demonstrated and cannot be denied, but In Transit focuses on the opportunities and unique experiences it afforded a number of extraordinary individuals to provide a fuller picture of Japanese colonial culture. By observing the empire—from Tokyo to remote Mongolia and colonial Taiwan, from the turn of the twentieth century to the postwar era—through the diverse perspectives of gender, the arts, and popular culture, it explores an area of colonial experience that straddles the public and the private, the national and the personal, thereby revealing a new aspect of the colonial condition and its postcolonial implications.