This article is about how Calcutta’s image as the world’s foremost crisis city was constructed from the mid-1950s, and how it came to be used by a broad political spectrum—from the American left and right to, allegedly, Fidel Castro—for rationalizing a variety of positions on urban development. This hyperreal Calcutta was the product of a global conjuncture which centred on Western, mainly American, anxieties about how large cities of the Global South could destabilize the postwar world order and development paradigms. It influenced global urban development by challenging the anti-urban bias of development institutions of the 1950s and bolstering the case for state-led interventions thereafter. However, from the mid-1970s, Calcutta’s ‘refusal to die’ became an example used by the American right to argue in favour of planned shrinkage and benign neglect of cities. Calcutta’s resonance in global debates on urban issues lay in the city’s confrontation with ‘life’ and ‘death’ which helped mask divisive issues such as race and immigration in discussions about American and Western cities.