This thesis explores the correlation between representation of the adolescent male in late twentieth-century fiction and the progressive disengagement of boys from the practice of reading during that same period. By mapping the fictional embodiment and re-mediation of juvenile male experience through a series of focused, yet interrelated studies of seminal works in the genre since 1950, the vital and often overlooked disjunction between the fictional and lived experience of adolescent males emerges as a definitive reason for the steadily diminishing number of young male fiction readers. Across the four case studies that comprise this thesis, the determining effects of habitus and field on teenage male engagement with young adult fiction are explored through analysis of mimetic limitations in key texts by prominent American authors, including J. D. Salinger, S. E. Hinton, Robert Cormier and Stephen Chbosky. In close reading and application of convergent methods drawn from cultural studies, cognitive narratology and theories of gendered reading, this thesis explores the complex divergences between fictional representations of male adolescence and the challenges presented by the efflorescence of other forms and channels of meaning-making for young males from 1950 to 2000, including a vast array of visual and digital media. Whilst selective, the case studies pay particular attention to shifts in language, narrative devices and literary techniques that have traditionally enabled teenage males to close the gap between the existential fuzziness of fiction and the physical manifestations of adolescence. Each case study embeds the works under discussion in their particular social and historical contexts, ranging from post-World War Il paranoia, evolving class structures and the emergence of feminism as a significant political force, to the rapid expansion of global capital and the unsettled political ambience generated by the Cold War. Themes of impermanence, intimacy, solipsism and isolation that typify young adult fiction in this period are also considered, particularly in relation to the ways in which the exemplary novels variously enact homosocial identifications and dynamics, and how this performative queering of masculine norms, in turn, informs the engagement of young male, and indeed, female readers in fictional incarnations of adolescent masculinity.