While Fitzgerald’s novel stands as testament to his engagement with and profound understanding of his historical and cultural milieu, this paper explores the critical question of visual representation of reality in the early twentieth century analyzing Gatsby’s impulse of self-transformation and the task of producing his new self which mark him indubitably an American figure. Focusing on Gatsby’s paradoxical “new” identity which is at once exalted and impoverished in the novel, this paper examines what means for a new identity, a change, a transformation or self-invention to be displayed in The Great Gatsby and how Fitzgerald responds to the cultural discussions of the time, that is, the contradictions and controversies of the representational possibilities that inform a radical re-conception of the process of American identity in the modern era. As an extension, this paper examines Nick’s visual narrative, which serves as a medium of truth and revelation and complicates the construction of Gatsby’s reality. In fact, Nick’s framing the world of Gatsby in vision which mediates between Gatsby’s world and our perceptions of it is always retrospective and insidiously contextualized. Therefore, when Nick’s visual sensibility creates its own patterns of meaning and significance, the ubiquity of visual images is more likely to exacerbate the confusion between reality and illusion as well as the disparity between the representation and the real. And it lends a critical weight to the conflict between authenticity and imitation, fact and fiction, representation and the real, subject and image, reality and illusion. Paying particular attention to Nick’s narrative, this paper also discloses how Nick’s manipulation of the visual in his narrative, that is, his re-creation or re-presentation of Jay Gatsby in vision, enhances the novel’s ambiguity and contributes to the novel’s ideological construction of meanings, values, norms, and beliefs.