The prominence of the term ‘Postmodernism’ in critical responses to the work of Alasdair Gray has often appeared at odds with Gray’s own writing, both in his commitment to seemingly non-postmodernist concerns and his own repeatedly stated rejection of the label. In order to better understand Gray’s relationship to postmodernism, this thesis begins by outlining Gray’s reservations in this regard. Principally, this is taken as the result of his concerns over the academic appropriation of his work, and his suggestion that ‘postmodernism’ is an entity wholly constructed and primarily active within critical theory, with a tendency to elide the political dimension of literature under its own assumed apolitical solipsism. While acknowledging these reservations, this thesis goes on to explore the extent to which theories elaborated under the ‘postmodern’ heading possess utility as an approach to Gray’s work, primarily focussing on the extent to which they necessarily stand at odds with his political concerns. To this end, subsequent chapters go on to read Gray’s major works in parallel with appropriate theoretical models drawn from the diverse configurations given postmodernism. Comparison between Gray’s project in Lanark of providing contemporary Glasgow with imaginative depiction and the cognitive mapping demanded in Fredric Jameson’s account of the postmodern not only highlights their similarities, but identifies this notion of the ‘epic map’ as a central aspect of the political dimension of Gray’s writing. The ‘epic map’ recurs in consideration of 1982, Janine, which explores the potential political agenda in its narrators’ seemingly postmodern fabulism, and its relationship to seemingly less ‘postmodern’ concerns of the novellas The Fall Of Kelvin Walker, McGrotty and Ludmilla and Something Leather. Likewise, ‘mapping’ also plays a part in approaching Poor Things in the context of postmodern historiography as described by Jameson and Linda Hutcheon. The penultimate chapter explores A History Maker as a complex negotiation with the very notion of postmodernism, installing, rejecting and subverting tropes drawn from postmodern theories, principally those of Fukuyama, Baudrillard and Jameson. In the concluding chapter, while no final conclusion is reached regarding a fixed relationship between Gray and the postmodern – a notion taken as impossible, given the heterogeneity of the values ascribed to the term – a degree of utility, and certainly of relevance, in approaching even Gray’s political concerns is thus established.