Living in the spectacle of Hong Kong's skyscape, how often do its dwellers actually see, not to mention reach, its rooftops? Intriguingly, despite their apparent ephemerality and inaccessibility, the vertical fringes of the city feature frequently in Hong Kong cinema: the rooftop. In this article, we connect the cinematic trope of the rooftop to the anxiety of living in a postmetropolitan city like Hong Kong. We do so by walking with Georg Simmel's blase attitude and Benjamin's flanerie in the metropolitan city, to meet Christoph Lindner's more (self-)destructive blase individual trying to grapple with his postmetropolitan anxiety. Finally, we posit to understand the deployment of rooftops in Hong Kong cinema - in the crime thriller Infernal Affairs, the coming-of-age drama High Noon and the psychological horror Inner Senses - as a way out, literally and figuratively, a space where one negotiates and perhaps overcomes a blase postmetropolitan individuality with moments of radical reconnection.