The aim of this paper is to explore the visual, sensory, and performative dimensions of urbanism through photography, focusing on the works of Swedish and East German artists such as Ann-Christine Jansson (b. 1950), George Oddner (1927–2007), Roger Melis (1940–2009), and Helga Paris (1938–2024). These artists are united by their commitment to photorealism and their ability to document reality without embellishment. In the GDR, Melis and Paris captured subjects that defied the official aesthetic, such as empty shops in derelict buildings in Prenzlauer Berg or abandoned car wrecks along Friedrichshain’s streets—images that spoke of decay and scarcity rather than progress. Similarly, Oddner documented the social and aesthetic dimensions of Malmö’s Million Programme in his project Ugly City (“Ful Stad”), capturing the unvarnished realities of life in high-rise developments. George Oddner’s style as a photographer is characterized by a sharp eye for detail, a profound sense of composition, and an ability to capture the humanity in his subjects. His work often blends documentary realism with an almost poetic sensibility, revealing the beauty in ordinary moments. What connects their work is a rejection of idealization, a sharp political sensibility, an ethnographic curiosity about everyday life, and a subtle, often wry sense of humor. They invite critical reflection on the evolution of high-rise architecture in Sweden and the GDR prior to 1989, as well as the ways these urban settings continue to shape collective memory, individual experience, and social visions in the present day.