Supported by a selection of original creative works, this thesis will undertake a comparative study of the ways in which masculinity is represented in David Foster Wallace’s Brief Interviews with Hideous Men and Chuck Palahniuk’s Fight Club. I will begin with an overview of the field of masculinity studies, outlining the theoretical underpinnings of this thesis and its situation within the wider scholarship. Via close textual analysis, this thesis will examine the machinations by which these texts’ characters resist the oppressive forces of hegemonic masculinity and how such resistance frequently reproduces the patterns of hegemonic masculinity and thereby reinforces its dominant position. The way in which both texts make use of fragmented form and style to reflect the fractured experience of those who occupy masculine identities will also be a significant point of discussion. This fractured experience, I will argue, results from dissonant social and cultural expectations and masculinity’s relationship with a complex modern world which induces a sense of dissociation, of disconnection in those who inhabit masculine identities. In concluding, I will suggest that both texts advocate the cultivation of bodily and sensory awareness as a means of combatting the dissociative effects of contemporary masculine experience, and of celebrating multiple, disseminated masculinities over hegemonic ideals.