Egypt’s capital has long captured the literary imagination of its writers. Throughout the first half of the twentieth century novelists and short story writers drew on the urban setting of Cairo in the development of these two relatively new literary genres, both part of a growing realist tradition. Cairo was the backdrop against which writers depicted the nation’s struggle against British colonialism, the possibilities of national independence, and the people’s confrontation with a rapidly changing world; in these works the city’s alleys and streets, its architecture and edifices, were as important as its inhabitants. This paper explores the representation of the city of Cairo in the work of the ‘Sixties Generation’ in Egypt, as a means to examine the socio-economic, political, and aesthetic changes of the post-colonial period. By proposing a reading of these works that concentrates on spatial representations, I emphasize an approach that attends to both literary innovation and thematic preoccupation. Through a reading of two novels by writers of this generation —Sonallah Ibrahim’s Tilka-l-ra?i?a (The Smell of It, 1966) and Gamal al-Ghitani’s Waqa?i? ?arat al-Za?farani (The Zafarani Files, 1976)— I argue that there is a move away from the realist depictions of the popular quarters of the city as the site of national struggle or of the alley as the cross-section of Cairene society. What we see instead is the reimagining of the urban landscape as a prison and the alley as a fantastical space. In this presentation I will demonstrate how each of these novels presents a different metonymic approach to the mapping of urban space revealing that the relationship between the individual and the state is one dominated by techniques of surveillance and repression. Within this context of state repression and surveillance, these novels launch virulent critiques against the regime of Gamal Abdel-Nasser, exposing the failure of the post-colonial state in Egypt in the years following the 1952 Revolution.