Freud’s 1914 paper “On Narcissism” is one of the most important papers of Freud’s time when considering the development and trajectory of his thought. Though many published works touch on this importance and examine details of development with which it is associated, a systematic review of the published literature reveals that no piece has yet brought all of these observations, critiques, and ideas together in one piece focused primarily on the theme of Narcissism within Freud’s work. Thus, this paper points out the transition of Freud’s portrayal of Narcissism from a two-person psychological model to a one-person psychology, while demonstrating how this transition engenders the expansion of the theory of ‘narcissistic object-choice, contributes to the development of the structural theory of the mind, a richer more complex conceptualization of the ego, the theory of the life and death instincts, and a refinement of his developmental theory of libido. This review and analysis leads to unique and new interpretations of the original texts and their context within the theoretical development. The paper should prove insightful for students and those who are relatively new to Freud’s work, as well as a streamlined, useful refresher for those well versed.