This article close-reads Modernist architect Ludwig Hilberseimer’s early architectural projects, which employed a language of uniform fenestration, repetition and geometrically reduced typical forms, as embodying Georg Simmel’s blasé attitude in analogical form, and places this reading in relation to Aldo Rossi’s concept of the analogical city and the political theorist Paolo Virno’s notion of the multitude. The first part outlines the discourse around Simmel, Hilberseimer and Rossi to note salient connections between these figures, their thought and the process of modernization. The second part discusses Simmel’s and Hilberseimer’s readings of the metropolis and interprets Hilberseimer’s formal language as embodying the blasé attitude. The third part places Hilberseimer in dialogue with Rossi and interprets Rossi’s analogical city as inhabited by another of Simmel’s figures, the stranger. The article concludes by tracing a line from Simmel’s figures of the blasé and the stranger via Hilberseimer’s metropolis architecture and Rossi’s analogical city toward the contemporary multitude, a collective linguistic subject. In doing so Hilberseimer’s and Rossi’s grammar of the metropolis can be rethought in relation to contemporary subject positions as a critical project toward an architectural theory of the multitude pushing back against the increasingly individualised city and market urbanism prevalent today.