In an age of technology, screens are all around us and hold great power in the shaping of public opinion and thought. The United States of America is the largest film industry in the world in terms of global box office revenue. Statistics show that in 2018, the United States had a gross box office revenue of 11.08 billion US dollars making it the leading film market in the world (Watson, 2019). American cinema has a strong influence on society’s notion of identity and what is accepted as the norm. This major research paper (MRP) uses a critical analysis of popular romantic comedies and coming of age films over the past four decades to explore the portrayal of masculinity as represented in Asian male characters within American cinema. Through the analysis of the films Sixteen Candles (1984), Joy Luck Club (1993), and Crazy Rich Asians (2018), I explore the traditional representation of hegemonic masculinity, the common elements of dominant portrayals of Asian men in American cinema, and how these portrayals have changed over time. This study examines the intersections of race, ethnicity, and gender drawing from a theoretical framework based on concepts of power and hegemony which shape mainstream notions of what being a man in society “really” means.