This article explores the representation of youth masculinity in contemporary Hollywood comedy. By focusing on the intersection of gender and generation, it emphasizes the importance of relationality in a consideration of representations of boyhood. Using Superbad as a case study, this article reveals the nuanced ways in which the crisis of masculinity is represented in popular culture in a postfeminist context. Foregrounding issues of homosociality in coming-of-age narratives, it emphasizes the tensions between generational expectations and performances of gender. Themes of loss and nostalgia are explored through analysis of the juxtaposition of adult and adolescent male characters in Superbad, providing insight into and understanding of the complexities of boyhood. Superbad is contextualized in relation to teen comedy more broadly, highlighting the important cultural space that contemporary Hollywood comedies play in (re)constructing discourses of masculinity.