The body of poetry and prose produced by Iain Sinclair between 1975 and 2002 represents a sustained engagement with the question of the role of art and literature in the representation and comprehension of the city. This thesis reads Sinclair's work as a political intervention in the relationship between literature, urban space, and history, and takes its theoretical stance from the body of critical approaches to the city first articulated in Walter Benjamin's Arcades Project. The thesis proceeds on a broadly temporal and geographical basis from the East End of the author's 1975 poetic work Lud Heat to the suburbs of the capital in 2002's London Orbital, and is split into three sections of two chapters each, entitled 'Form', 'Place', and 'Memory' respectively. This structure periodises the author's oeuvre, demonstrating the ways in which his work responds to a series of historically specific cultural and political constellations; the titles name the perennial themes and critical concerns of Sinclair's writing, and allow the investigation of the ways in which these are instantiated and elaborated in his texts.Sinclair's earliest work builds upon the formal innovations and ambition of modernist poetics. Through an analysis of his first major collection of poetry, Lud Heat (1975), and his first novel, White Chappell, Scarlet Tracings (1987), the first part of the thesis - 'Form' - argues that these texts constitute an interrogation of the institutions of literature in postwar Britain in the wake of what Peter Burger identifies as the failure of the historic avant-gardes. These opening two chapters contextualise Sinclair's work so as to reveal its anti-establishment, oppositional character; the second section of the thesis - 'Place' - moves on to examine how these concerns are expressed in relation to urban space. Chapter 3 turns to the figure of the flaneur in his second novel, Downriver(1991), and demonstrates how this work at once radically decentres this subjectivity and is conditioned by his limitations. Downriver marks a moment of political nihilism in Sinclair's work, neither able to bring to representation Fredric Jameson's aesthetic of 'cognitive mapping', nor the emancipatory potential of postmodernism. His later 'psychogeographic' writing articulates a response to this impasse: chapter 4 demonstrates the ways in which Sinclair's use of this term at once divests it of the utopian character of its Situationist origins and transforms it into a dissenting, heterogeneous, literary mode. The final two chapters - 'Memory' - investigate the political potentialities of the models of history expressed in Sinclair's work. Chapter 5 turns to the author's use of the Gothic in relation to Benjamin's 'messianic' notion of 'the what has been', and argues that whilst such strategies can be of great critical potential, they at once risk collusion with that which they attack. Chapter 6 then analyses 2002's London Orbital, and argues that this work's ironic, tentative nostalgia for both the author's anti-establishment past and for the utopian character of former socio-political projects represents an attempt to find a way beyond the political malaise that Sinclair's London corpus identifies.