Paul Ricoeur claims that it is on the scale of urbanism that we best catch sight of the work of time in space. This article establishes two paradigmatic ways of seeing time in the city, the synchronic urban gaze and the urban memorial gaze, in order to explore how visualisations of the cityscape of the former GDR negotiate the significance of obsolescence, both ideological and physical. These paradigmatic forms can be associated with the ‘official vision’ of the cityscape, and ‘alternative’ visions respectively. While the state vision is evident in its urban planning, and the visual discourses at its disposal, the alternative visions are expressed in forms of visual culture (film and photography) that also explicitly engage with the visual discourses of urbanism. The article thus begins with an analysis of the official vision, through a consideration of the demolition of the Berlin Stadtschloss in 1950 as an act that may have been underpinned by both the ideological and physical obsolescence of the Schloss, but was ultimately justified by the need to create urban space for ideologically-motivated circulation. It then charts the changing relationship to obsolescence on the part of the regime's urban planners in the late 1960s, showing how this ostensibly dovetails with alternative ‘subjective’ visions of the cityscape in the 1970s in films such as Die Legende von Paul und Paula and Solo Sunny, and in the photography of Ulrich Wüst. Such visions are widespread and largely permissible by the 1980s (with the notable exception of Helga Paris's study of Halle); and Peter Kahane's 1990s film, Die Architekten, is read as offering a summary of these positions, as well as of the tensions between official and alternative ways of framing the manifestation of time in the cityscape. The article concludes by considering the afterlife of the obsolescent cityscapes of the former capital of the GDR within the new ‘official’ regime of representation that dominates in the ‘new’ Berlin.