Taiwan’s some four hundred years history, culturally and politically, is inscribed by relationships between rulers and the ruled that shape its social sophistication and gaps between forms of high culture and popular culture. Its built environment, inevitably, echoes this complexity as a representation. Examining Taiwan’s very recent built environment, most critically, this phenomenon is highlighted by the uncertainty that translates Taiwan society’s anxiety about connecting the yet passed authoritarian past and the seemingly democratic present when its post-war Martial Law period was officially terminated in 1987. This paper observes the immediate historicity today in Taiwan that represents this uncertainty, through scrutinising different cultural forms which the built environment has been identically (re)represented. As a central argument, this paper schematises a context which mediates different spatial objects that are derived from different cultural political origins, literature and cinema, where as texts in one context could be relevant, contradictory or even parallel, and suggests a form of appropriate fuzziness. This form, unlike the social conundrum driven by the awkward cultural and political status of Taiwan society, through ways of urbanisation, geo-identification and spatial idealisation, has pinpointed the possibility that directs Taiwan’s spatial evolution on the road ahead.