This project explores the representation of white, American masculinity within the Hollywood bromantic comedy cycle. By analyzing three interrelated components (close homosociality, infantilization, and relationship to patriarchy) of the model of masculinity perpetuated by this cycle of films, this study reveals the hegemonic motives therein. Despite the representation of a masculinity nervously questioning its position within the romantic comedy narrative and the broader patriarchal structure, the results of this representation are, ultimately, regressive and reactionary. Cultural gains made concerning gender, sexuality, and race are doubled back upon in a cycle of films that appeal to regressive modes of misogyny, homophobia, and racism still present in Hollywood filmmaking, and the hegemony of white, patriarchal heteronormativity is rigorously maintained.