Role play prevails in our daily activities from working in a company to playing a videogame. In this regards, conceptualizing the role-play process helps us understand how people interact with other people in both face-to-face and computer-mediated environments, as well as how such social interactions could affect people's self-concept and corresponding behaviors in particular ways. The purpose of my dissertation is to propose a new theoretical model of role play to explicate our virtual experience in media, to discuss theoretical implications of the model, and to provide empirical evidence for the utility of the role play perspective in understanding the effects of role enactment in interactive media. In the first three chapters I discuss a new theoretical framework for the multi-layering model of role enactment. Particularly, I review the literature on social psychology and communication to address the prevalence of role play in our daily activities and the relationship between role play and changes in the self-concept and behaviors in Chapter 1. In Chapter 2, I conceptualize a multi-layering model of role enactment and explain how we engage in role play in videogames based on Clark's multi-layering model (Clark, 1996) and Leslie's metarepresentations (Leslie, 1987). In Chapter 3, I elaborate more on the multi-layering model of role play to enhance our understandings of entertainment experience based on the review of important aspects from the seven entertainment theories. In the final chapter, I report on the results of two experiments in order to provide preliminary empirical evidence to support the utility of the role-play perspective. Not only do the results confirm the usefulness of a new role-play perspective to understand our psychological and behavioral reactions from the role enactment in interactive media, but also they suggest that altering contextual features of interactive media could influence the degree to which people conform to role play. Theoretical implications as well as practical strategies for the design of interfaces for interactive media (e.g., virtual reality systems and videogames) are discussed.