The recent flurry of research about arts‐led regeneration initiatives illuminates how contemporary arts festivals can become complicit in the production of urban inequality. But researchers rarely engage with detailed empirical examples that shed light on the contradictory role that artists sometimes play within these spectacularized events. Similar research in performance studies connects the political limits and potential of social practice arts — interventions that encourage artists and non‐artists to co‐produce work — as civic boosters strive to stage cities in order to attract investment. In this article, I explore the case study of Streetscape: Living Space at Regent Park, a participatory artistic intervention programmed in a public housing neighbourhood that is undergoing redevelopment in Toronto, Canada. Streetscape was part of the Luminato festival, an elite booster coalition‐led festival of ‘creativity’. I refer to these arts interventions to demonstrate how artists engaging in social practice arts can become complicit in naturalizing colonial gentrification processes at multiple scales. But I also reveal how artists can leverage heterogeneous arts‐led regeneration strategies to make space for ‘radical social praxis’ (Kwon, 2004), interventions that challenge hegemonic regimes. I conclude by interrogating the effectiveness of place‐based efforts in unsettling the ‘creative city’.