In this PhD project, my research questions explore the similarities in the historical, social, and cultural evolution of Glasgow and Genoa, and how these have articulated, and been informed by, the literary portrayals of these post-industrial cities. This study interprets the urban phenomena depicted in prominent late twentieth-century literary works. It discusses and compares the writing of Scottish authors Alasdair Gray (1934-2019) and James Kelman (1946-) with the poetry of Italian authors Eugenio Montale (1896-1981), Edoardo Sanguineti (1930-2010), and singer-songwriter Fabrizio De André (1940-1999). The investigation highlights the similarities in the historical evolution of the Scottish and Italian cities seen through the lens of site-specific literary works. This affords a better understanding of how the urban context might have conditioned the literary production of the authors, and evidences the active participation of urban literature in the city’s transformations through the assessment of tangible interventions upon the social and civic realms. The research also affords a meticulous appraisal of the relevant theoretical criticism associated with pertinent works that engender the character of the two cultural geographies from which they emerged. Glasgow and Genoa share momentous histories as shipbuilding powerhouses, progressive demographic declines, and strategies of re-branding as cities of culture. The primary objective is to establish that their parallel development might also have laid the foundations of an unwritten kinship and/or cultural sensibility. By way of a resilient and proud industrial heritage, this is demonstrably embodied in both cities’ essential identity. An area of specific interest is the holistic evaluation of the means through which metropolitan structures can influence and shape fictional narratives within the cultural paradigm (e.g. Gray’s' better nation' trope). An auxiliary and critical role is played by the contrasting topographical condition of the two cities. This is measured by the theoretical adoption of cross-sections as the explanatory graphical component of the pre-eminently vertical organization of Genoa, in juxtaposition with the horizontal layout of Glasgow, signally intelligible through the map, a pictorial delineation of the urban space reliant on a two-dimensional plan drawing. The Nolli Plan(1748), devised by Giambattista Nolli for Rome, is particularly suited to study the urban configuration of Glasgow, as it is a mode of diagrammatic representation which centres on the expression of figure-ground solids and voids. The existing theoretical framework comprises sociology, New Materialism, embodied geography, and the spatial turn, as well as psychoanalytical theory, literary studies, and Marxist humanism. The chosen methodology blends the scrutiny of archival materials, field research (case studies5and artefact analyses), and a phenomenologically-orientated approach grounded on the experience of space and place. The regions of scholarly investigation encompass the dialogue between the real and textual dimensions, spatial movements and ontological positioning, comparative epistemologies, and the literary word understood as a political act, with its capacity to represent and/or knowingly misrepresent the cities' civic and social identities.