In this essay, I examine how glass is played and how urbanites are ＂played＂ by glass in Jacques Tati's film Playtime, in which the protagonist Hulot and a group of American tourists get lost in a world of transparency and reflection. Since its emergence in the late 19th century, glass has transformed our cityscapes, our perceptions of space, and our interactions with the material world. Glass is unique in the sense that it can be both medium and barrier, and thus conveniently becomes a rich source of metaphors that refract the complexities and paradoxes of modern urban life. Using glass as a device and a trope, Tati criticizes the unpleasant uniformity of the cityscape and how glass contributes to further the ambiguity of space and produces false impression and misrecognition. Drawing on Benjamin's ＂reception in the state of distraction,＂ I discuss how the viewing experience of Playtimes parallels the urban experience full of unfocused chaos, making the film itself mirror-like. Despite Tati's critique of the transparent glass labyrinth in Playtime, he seems to acknowledge the productive nature of glass, which is a perfect medium for capturing the transience and the uncanny in the modern urban experience.