German philosopher Walter Benjamin developed a creative field, a field beyond traditional science. His thoughts include philosophy, literature, culture, images of city space, and private essays. It is impossible to simplify these into one category. Based on variety of his thoughts, this paper intends to understand Benjamin's concept of image and its temporality. Benjamin's concept “thought-in-image” can be seen in various places. The concept “image-as-thought” is also developed everywhere. Image is however, always something more than just a representation to Benjamin. The concept of similarity, Mimesis goes far beyond being just identical while Allegory represents some kind of ‘absence'. However, no research has been conducted on the fundamental idea of thoughts on image that is developed through complicated phases. This paper attempts to discuss concepts of image that is presented through Benjamin's work: from Benjamin's language theory, The Origin of German Tragic Drama and his further similarity theory, One-Way Street, Arcade Project. This disputation can contribute a highlight to Benjamin's theory. Moreover, the question of what an image is cannot be separated from the question of language. Especially nowadays, in the world of contemporary Art and Culture, it is essential to question where this kind of aesthetics can fit in.