While Renaissance paintings were created around a fixed vanishing point, traditional Eastern paintings were drafted without linear perspectives. In Chinese and Japanese masterpieces, architecture and urban scenes are organized in unfolding parallel projections instigating a moving onlooker and a decentralized perception, while the inclusion of ambient environments epitomized in depictions of clouds intentionally blurs the whereabouts of the beholder. Starting from analyzing Eastern paintings, this paper proposes that not only do these paintings embody a different technique of representation, but they also foretell a distinctive mode of experiencing urban space inherent in Eastern contexts. Through analyzing films and video art, this paper dissects different screening practices that reorganize vision in a space sans-horizon. It extends its analysis from ancient art to an investigation of modern and contemporary urban milieu in East Asia. It argues that the frame of mind insinuated in these paintings has given rise to a profusion of screen-generated mediascapes in cities such as Tokyo; unlike western movie screens, urban screens in East Asian cities serve more purposes than a neutral interface of display. They destabilize spatiotemporal determinacy to engender an entwined system of plurality. They provide ambiences for city dwellers on-the-move, who unconsciously participate in urban rhythms through low-affect sociality. Finally, this paper uses those existing phenomena to speculate on a new mode of engaging with cities through advanced technologies such as the screening technique provided by Apple’s Vision Pro, while simultaneously bringing attention to overlooked urban problems in trends of globalization. The goal is to tease out a new form of spatial condition nowadays that could have an alternative history lodged in another cultural heritage and to explore the implications of a destabilized horizon in contemporary societies.