In this article I discuss 1980s New York cinema through the conceptual lens of landscape, drawing in particular on the interconnected but separate traditions of the pastoral and the picturesque. While the former mode of representing landscape is idealizing (the shepherd/nymph‐motif), the latter with its origins in the period of the enclosures of the English countryside tends to aestheticize poverty and dispossession. This distinction can productively be deployed in relation to tensions between glamorization and exploitation in 1980s New York cinema, which often dealt with the themes of rent, eviction, and unemployment in postindustrial settings. Focusing in particular on Downtown 81 (Edo Bertoglio, 1981/2000) and Desperately Seeking Susan (Susan Seidelman, 1985), I argue that the current nostalgia for a pre‐gentrified and less regulated New York in popular culture is dependent on these idealizing and aestheticizing tendencies insofar that they conceal or prettify some of the darker aspects of the period.