This paper begins with an exploration of the notion of the 'cosmopolitan'—as an ideal, a desirable goal, a dream on the one hand, and its politics, elitism and neo-liberalism on the other. Cast as the humanist counterpart of globalisation, cosmopolitanism has been inserted back into discussions on multicultural societies and emergent civil spaces as these become reconfigured by transnationalism and as the accompanying influx of transmigrants begin to trouble notions of the national self. The paper goes on to contextualise these debates in Singapore, a 'wannabe global city'. It examines the project of constructing a 'cosmopolitan' and 'creative' global city in Singapore—a 'cosmopolis' and clarifies specifically what ideas and strategies are being invoked by the terms 'cosmopolis' and 'cosmopolitan', catchphrases which litter government pronouncements on visions and plans for Singapore. The next section of the paper explores the uneasy fit between, on the one hand, the cosmopolitan gloss and, on the other hand, the older stance of multi racialism and the nation-building quest to construct a social fabric undergirded by a carefully calibrated racial arithmetic, a founding ideology which lies at the core of government policies since independence. It is also suggested that some of the elements of cosmopolitanism have its antecedents in the colonial era, although clearly the debates and assumptions (leading to a lack of debate) have shifted considerably. The paper goes on to examine the 'feel on the ground' and the extent to which government-inspired and articulated visions of a cosmopolitan future resonate with ground realities. This is achieved by interrogating the politics of inclusion and exclusion in the emergent discourses on cosmopolitanism and the 'place' of particular transmigrant groups in the city.