In the summer of 1928 in Berlin, the noted German Jewish philosopher Walter Benjamin (1892–1940) and Chinese American actress Anna May Wong (1905–1961) shared an unlikely encounter that set in relief European and American conceptions of modernity as well as white European intellectual and American racial minority cosmopolitanisms. On July 6, 1928, Benjamin published the results as “Gespräch mit Anne May Wong” [“Speaking with Anna May Wong: A Chinoiserie from the Old West”] on the front page of the leading German literary review, Die Literarische Welt. Read against a cache of Wong’s writings, the encounter and the writings are significant for how they intervene in constructions of cosmopolitanism and racial and gendered difference. This encounter raises questions concerning the relationship between Asian America, modernity, race, gender, and cosmopolitanism, linking notions of cosmopolitanism to a discourse of race in the transnational American context. Benjamin’s struggles in fully characterizing Wong also point to the antagonism between racialized American modern femininity and Eurocentric cosmopolitanism.