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This study proposes to contrast Walter Benjamin’s theoretical views of the everyday life of modern metropoli with those of Kon Wajiro. In the middle of the 19th century, as part of the era’s accelerated modernity, a completely new type of metropolis emerged. The emergence transformed the lives of modern metropolitans, and this was understood at the time by some to be problematic. In the early 20th century, Benjamin focused critical attention toward Paris while, on the other side of the globe, Kon explored and examined Tokyo. Benjamin outlines his observations in the Arcade Project, while Kon presents “modernologie” as a method by which to capture the modern customs of Tokyo. Both approach their respective cities from a microscopic (rather than macroscopic) point of view. Even though situated in the same historical moment with similar research agendas, it seems that little cross-cultural comparative analysis connects Benjamin with Wajiro. This study raises the possibility of shifting beyond East-West discursive dichotomies, and attempts to broaden the horizons of an Eastern-Western comparative literature by synthesizing and synergizing the similarities and differences between Benjamin and Kon’s theorizations.