The periodic summarization of Tokyo's characteristic after the modern era is as follows. In the Ages of Meiji, Tokyo became the official capital city and executed various functions as a modern city. During Taisho Age, with the vast increase of city population, it was developing into a mass production/ mass consuming city, until the Great Kanto earthquake destroys everything. Showa Age is when it becomes a full scale modern city after adopting the reconstruction system. This article intends to examine the Imaginative Geography of Japanese during Early Showa and Representation of Tokyo as it was understood in general perspective of the ages mentioned above. Specifically, it will study the intimate relationship between modern Tokyo and the literary men who have lived in it, and their literary expressions, by looking into literary men like Nagai Gahu or high class city residents in intelligent level, residents like office workers illustrated by a modern author such as Ryutanji Ryu, lower middle class residents appearing in Hayashi Humiko's autobiographical novel, and laborers and lower classes as illustrated in various reportages.