The article explores the display mechanisms of the postmodern city as a text in Serhiy Zhadan’s works during the period between 2008 up to 2022. We’ve investigated the city representation tools portrayed in the diachronic aspect. There have been studies of Ukrainian urbanism time-space and audio characteristics, viewed through the connection with European urbanity on the examples of Kharkiv regional centers’ and Voroshilovgrad depictions, the east of Ukraine urban points of district significance, as well as particular foreign urban locations. The purpose of the research paper is to distinguish and analyze the main categories of the Postmodern city as a text in poetry and prose by Serhiy Zhadan. The tasks of the research are focused on the definition and interpretation of the modern research methods within the investigation of the ‘the urban text’ category, the identification of the fundamental content-representative elements of the Eastern Ukrainian cities significant to the author, the interpretation of the main categories of the city as a text, and Kharkiv as a text in particular, in the creative heritage of the author. The research methods include hermeneutical, historical, literary, cultural methods and the method of contextual analysis. As a result of the study, it has been proved that the city text in Serhiy Zhadan’s works is represented by multiple forms, as well as the paradigm “the past – the present – the mixture of the past / the present”. The chronotopic skeleton of the city is embodied in a number of material congestions, represented by the intervened example of architecture, which bears the imprint of different historical eras. The urban chronotope is marked by location points, endemic for the writer: numerous spatial models of the railway stations, representing a gallery of social characters and algorithms of criminal schemes; bus routes, city transport, personified and serving as the “bodily organs” of the city; industrial facilities; monuments to Soviet leaders; hotels; zoo-images. A characteristic feature of destabilization is the depiction of the marginal components of the city (drunkards, drug addicts, prostitutes, dishonest politicians). The hotels serve as the points of sin and the marks of well-being. Serhiy Zhadan’s text is coded, symbolic, and is socially marked. The accompanying fragments of the realistic depiction are music, dances, weather, color, natural and unnatural sounds. The cities, marked by the influence of the historic shifts, create a picture of a transitional period in Ukrainian society. The frozen reality of the post-Soviet reality, embodied in the cities, reaches the peak of its transformation during the military conflict, which defaces the body of the city and modifies the mentality of its inhabitants. The buildings, the animals, the natural world tend to echo the military events and reflect the gradual degeneration and altogether rebirth of the city of Kharkiv. The urban space by Serhiy Zhadan is a mocking festivity. It revolves around day-to-day reality with the print of the epoch that dominates. The city by the author acquires the features of the whore-city. Serhiy Zhadan also generates a number of fresh or updated forms like city-orphan, city-cripple, city-mechanism, city-animal. The Ukrainian cities in the writer’s legacy are of male gender, whereas the foreign ones acquire noticeable female Biblical features. Thus, the Postmodern urban text as a holistic system of images and signs reflecting the specificity of the post-totalitarian urban culture gets formed in the writings by Serhiy Zhadan. The poetics of the Postmodern urban text by Zhadan enclude the intertextual devices; parodic and ironic reasoning of the traditional cultural archetypes (the sun-city, the city-whore, the garden-city, etc.) and their substitution with the new connotations (the city-dog, the city-fish, the city-ghost, the city-mechanism, the city-cripple, the city-orphan, the city of whores, etc.); the motif of escapism; fragmentation of depiction; the mode of a game with a reader. The works of the writer create the image of the Postmodern urban mind as nomadic, shelterless and carnival. This type of mind serves as a basis of a new peculiar type of a character formation – the eternal nomad-wanderer.