Fifty years after the first solo exhibition by photorealist painter Richard Estes at the Allan Stone Gallery, New York, this text proposes a reading based on the representation of the city, the installation of the concept of modernity and its critical scope. The introduction develops a bibliographical discussion based on the precepts of Charles Baudelaire and his vision of the modern city mediated by painting. In addition, the critic of the German philosopher Georg Simmel to the processes of modernization of Berlin at the beginning of the XX century and its incidence in the social life. From this perspective, the work of Richard Estes is analyzed emphasizing the idea of an uprooted dwelling of the illusory city present in his pictorial proposal: The photographic frames, the technical virtuosity in the translation of the materials and the representation of the uninhabited city, are developed in a reading of the artist’s work. The most relevant conclusions highlight the coincidences of the critical tradition of modernity developed in Europe towards the end of the nineteenth and the beginning of the twentieth, this time in a late-modern context expressed in the painting of Richard Estes.