Canonical representation and critical appraisal of urban Scottish literature before the publication of Alasdair Gray’s Lanark, in 1981, emphasizes its innate realism. This realist reading pays attention to surfaces and objective identities, rather than subjective depths and transgressive or transcendent possibilities. It inevitably encounters areas of lack, absence and failure. This thesis proposes that the Scottish representation of the city, as in other literatures, is inextricable from its perception and subjectification. This thesis explores a number of non-realist readings and attempts to open up the realist surfaces. These opening strategies are prompted by the phenomenological and intertextual readings demanded by the works of Alexander Trocchi. Trocchi can be considered the linchpin in a body of urban literature that is concerned with transgressive modes of self-realization. From his pivotal position a line of inheritance may be drawn back to the male-authored urban visions of James Thomson and John Davidson, and forward to Irvine Welsh. In the ‘metaphysical’ readings suggested in this thesis, the narrative delineates a quest for transcendence, catalysed by the protagonist’s recognition of lack at a realist level and his desire for meaning within metaphysical or psychological depth. Thus, the city may represent a real place and ask for a realist reading, but it also functions as the controlling metaphor for concerns pertaining to personal identity. The city is a psychogeographical terrain that embodies an interplay between reality and the ideal. In the abject topos of the city, however, the dialectic of transcendence does not move toward totality of vision, or unity of identity. Negative and transgressive modes such as rupture and division are recuperated to engender a conception of transcendence based on ‘becoming’ and movement, rather than on a place or state of being. The principle aim of this thesis is to address a shortfall in analytical criticism on the body of Scottish urban literature. It traces the representation of the city from nineteenth-century social and religious tracts, poetry and fantasy texts and suggests that such works are more appropriate forerunners to the modern urban Scottish novel than the sentimental and lightly humorous novels and stories of the so-called ‘urban kailyard’. The tenets propounded in these early works are developed in a theme-driven analysis of Scottish canonical twentieth-century urban novels. Revisionary readings and recontextualization of these works, based on modernist and Continental literary and philosophical paradigms, aim to reappraise a hitherto disregarded tradition out of which has developed the recent flourishing of late twentieth-century Scottish writing.