In the twentieth and twenty-first centuries, literary representation of the city has proliferated as it becomes a central factor in constructing modern literature and postmodern literature. The contemporary city reflectspostmodern reality in which “the world itself becomes both discontinuous and indeterminate” (Lehan, 1998, p. 267). In postmodern literature, the city is complicated and diverse, of diminished humanity and human isolation and anxiety. This paper aims to investigate the complex urban zone of the contemporary city as reflected in the postmodern novel NW (2012) by the British writer of Jamaican origin, Zadie Smith. The paper attempts to answer the following questions: Does the city as a trope in postmodern literature become an equivalent to entrapment? How is the city transformed into a system of signs that cannot be deciphered? How is the construction of subjectivity affected by the postmodern city? To answer these questions, the study will employ Richard Lehan’s theorization of the postmodern city and the subject in addition to Jean Baudrillard’s theory of hyperreality as a theoretical framework. These theories will be utilized to analyze the symbolic representation of city in literature as reflected in NW. By integrating postmodern theory and literary analysis, this research seeks to fill the gap by focusing on the psychological weight that the postmodern city exerts on the individual. By integrating postmodern theory and literary analysis of Smith’s fragmented characters, this research aims to contribute to the understanding of the complex relationship between urban spaces, their literary portrayals, and postmodern literature.