In response to debates on emergent and rogue forms of urbanism that are reshaping the African city, this article examines the night‐time leisure economy as one particular social context in which the tensions and opposition between regulation/deregulation and informality play out. This article shows how ideas that centre on Northern entertainment spaces and drinking venues (bound with policy initiatives to reposition the city) have come to inform policy initiatives to regulate working‐class public spaces in South African cities with the objective of controlling unruliness. Through a case study of informal and illegal drinking venues in Sweet Home Farm, a slum settlement in Cape Town, we provide an insight into the ways in which people seek to reclaim social space and impose their own vision of the creative city. The article demonstrates that while illegal drinking venues can be imagined as ‘unruly, unpredictable, surprising [and] confounding’, they are characterized by a responsive agility to the social, cultural and physical environment. We argue that the capacity and tenacity of informal drinking venues to adapt to regulatory pressures present a range of possibilities for reimaging the night‐time leisure economy in ways that are inclusive of the poor and conducive to negotiation.