This paper examines the real and virtue figures of the modern city as written from the viewpoint of the shadows of the city. This study examines this theme as evidenced in various literary works, in particular that written by Chamisso as well as others. Such a theme in literature became prominent from the 19th Century as the urban "city" emerged as a gathering place for the masses. The first urban "city" is recognized to be Paris, and it is noted that those living in the city possessed both "front" and "back" faces. This characteristic of the population caused a differentiation between the urban city environment and the rural countryside. The literature that emerged depicting this societal transition in the 19th Century illustrated a difference between the self and the shadow, where the shadow possessed no will in its existence but existed in subjugated relationship with the self. Without the existence of the self, the shadow could not exist. This idea shifted in the 20th Century, and the self and the shadow became separate entities or ideas where no subjugation of the shadow existed. It is highly possible than in the future, the relationship between the shadow and the self will further develop where the self is lost within the virtual shadow of the post-modern city.