Film has taken a uniquely powerful presence within human culture. Film is a powerful means for the conveyance of; culture, learning, relaxation and ideologies (Giroux, 2001). Film is therefore a powerful tool to assess the ordering of masculine representations and place masculinity in an historical context (Leiner, 2004). The film Harold and Kumar go to White Castle (Leiner, 2004) deals with several masculinities in relation to the ideal of hegemonic masculinity. Connell (2005) sees that the hegemonic masculine stereotype and the marginalised masculinities and countertypes are very present in all levels of society. Hegemonic masculinity is unattainable ideals about true male behaviour, what a true masculine male entails, and reductionist assumptions about countertypes. However, masculinity is not only a set of features a man should possess (Connell, 2005). I will study gender images and engendered practices that emerged out of colonialism and outlived the era of colonialism in Anglophone film. I claim that colonial representations of masculinity are still present in film. My question is; How does the movie Harold and Kumar go to white castle use representations of maleness stemming out of a colonial ordering of masculinity and representations of marginalised masculinity. The negotiations on the gender, sexuality, race and class intersections in society create formations of different stereotypes about the essence of those masculinities and femininities. Hegemonic masculinity and the marginalised masculinities and countertypes are a social construction and only make sense in the cultural and historical framework (Connell, 2005). Mosse in his book The Image of Man gives a historic account on the ideal of manliness. Not as a single defined idea of masculinity, but the different characteristics and qualities that a man should possess in a particular crossroad of differences. However, the use of masculinities always involves simplification (Mosse, 1996). Said (1979) in his famous book Orientalism made the Western imposition visible on culture and the erroneous suppositions which are at the core of Western attitudes toward the Middle East (orient) (Said, 1979). Gender is another construction with underlying assumptions about what it entails in essence to be a male and female. Isaac and Mercer (1988) argue that one cannot separate ethnicity from masculinity. The social construction of manhood influences the historical context it developed in (Mercer & Isaac, 1988). The structure of the series is the following; first, the concept of masculinity is discussed. Second, the connection between colonialism and masculinity is established. Third the role of marginal colonial masculinity in Hollywood movies is analysed. The use of gendered stereotypical images in film has a long standing connection. Fourth, the masculinities in the movie Harold and Kumar go to white castle (2004) are analysed and placed in the colonial context. In order to confirm the ideal of the hegemonic male's superiority or his masculinity, the marginalised masculinity is shown as conquered or lacking.