The paper analyzes five movies from Macedonian cinematography, which show the changes in the representation of the city of Skopje in the period after the earthquake in 1963 until today. It shows how historical, socio-political and ideological changes have affected the architecture, urban landscape and identity of the city. The changes start with the reconstruction after the earthquake in 1963, which reflected the brutalist architecture, visible in the movies Skopje 63 and Memento, movies that affirmed socialist values. At the same time, there is a gradual penetration of capitalism from the West and the development of the consumer society. The conflict between the blocks in the movie Hi-fi is portrayed as an intergenerational conflict between a father and his son, who are representatives of their conflicting values. The modern city of the 1980s in the film Upside Down is portrayed through the flȃneur (a wandering city walker), depicting the hopelessness, rebellion and disorientation of society at the time. Today's picture of the city and the identity of society is influenced by memories of traumas from the past, specifically the Second World War, which are problematized in the movies Memento and The Third Half. The latter movie shows a city that is the result of the Skopje 2014 Project, which imposes a fictional tradition on citizens. The analyzed movies point to the crucial role of citizens in the construction of their own memories and their resistance to imposed policies of memory, thus deciding what will become part of their identity and the identity of the city of Skopje.