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Constant Nieuwenhuys (aka Constant), twentieth-century painter and architect and founding member of the Situationist International, is perhaps best known for his ambitious project of unitary urbanism, New Babylon, on which he worked from 1958 until 1973. This proposed city (which would, theoretically, cover the globe) was intended to prompt all people to express their creativity through their constant reconfiguration of its open and malleable living space. Explicitly designed for homo ludens, in it social life was to be constituted by architectural play. But, as Mark Wigley has noted, “play was the whole point of New Babylon but not its mode of production”. As designer of this universalizing and revolutionary play-space, Constant’s role entailed the contrivance of open-endedness, and thus implicitly relied upon the very artistic authority that the Situationists had rejected (Constant left the Situationists in 1960). Today, 50 years after he began his project, we can witness similar ideals and contradictions in the virtual world Second Life, an architected social space which also claims to be an infinitely malleable forum for creative expression. In this article the author traces to what extent the ideological foundations of both of these projects can be linked to postwar attitudes toward technology and authority on both sides of the Atlantic, and explores how they each draw on notions of play in distinctive ways. Arriving at the same ideals and contradictions via separate but related paths, New Babylon and Second Life reflect two responses to the challenges of design and post-bureaucratic hopes for the productivity of play.