(Hyper)masculinity is a universal and ostensibly rewarding concept, but only when performed within cultural limits. If these limits are violated, hypermasculine performances cease to be rewarding and instead begin to subvert the norms they are designed to uphold. Such destabilising performances are found in transgressive fiction, a genre that seeks to contravene cultural norms and taboos via extremely violent or sexual performances. While transgressive fictions often incorporate various physical and sexual behaviours that code conventional representations of masculinity, they derive much of their narrative energy from the subversion of those very conventions. Using Hubert Selby Jr.’s Last Exit to Brooklyn (1957), Iain Banks’s The Wasp Factory (1984), Bret Easton Ellis’s American Psycho (1991), and Chuck Palahniuk’s Fight Club (1996) as examples, this thesis will argue that the conjunction of transgression and (hyper)masculinity has the potential to expose and satirise sociocultural structures of meaning. Firstly, this thesis will demonstrate how transgressive texts subvert language by challenging the signifying power of (hyper)masculine speech; secondly, it will discuss the purpose of rituals in affirming masculine norms, and show how transgressive fictions undermine this purpose by stripping ritualistic performances of their legitimising potential; thirdly, it will demonstrate how representations of transgressive hypermasculinity foreground heterosexual masculinity as mimesis while simultaneously exposing its futile suppression of homosocial or conventionally feminine drives. Finally, it will show how transgressive narratives prompt a reading of masculinity as inherently problematic by detaching (hyper)masculine performances from conventional rewards and resolutions.