This thesis examines representations of masculinity in post-2000 Hollywood film and critically reports what these films reveal about the current crisis of masculinity. The major domains for this analysis are representations of the body, technology and violence as they relate to masculinity. These representations are considered using social and psychological theories, as well as film and gender studies to make the findings relevant on a psycho-social level. This thesis explores a lack of intimacy between men and others, seen as a failure to secure satisfaction through traditional ideals of masculinity. This study also considers the commodification of the body which creates a malaise that fails to solve related issues of personal happiness and social relations. Further analysis reveals representations that suggest technology steps in to provide a 21st century solution to a lack of intimacy, failing to recuperate the loss in personal relations. Lastly, violence is represented as another failed masculine solution. The focus is on the consequences of the violence, rather than the violence itself. These representations question and query hegemonic masculinity and reflect significant issues relating to the crisis of masculinity in the post-2000 era.