Coastal cities have increasingly welcomed initiatives for producing temporary urban art spaces to lure tourists and revitalize the local economy. This article examines the under-explored contested relationships between a major temporary art event and social (dis)engagement in the context of coastal urban regeneration. During the pop-up art event Dismaland (2015), led by the reputed graffiti artist Banksy and company, the coastal resort of Weston-super-Mare in England experienced an upsurge of international visitors. Banksy envisaged this ÒBemusement ParkÓ, situated in an abandoned lido, as an antagonist twist of Disneyland and the commercial modus operandus of theme parks. Drawing on discourse analysis of expert and public perspectives and autoethnographic experience, this article challenges the experienced extent of antagonistic art practice in juxtaposition to the formal discourse of creators and urban policymakers. The examination of the event's artistic, behavioral, spatial and temporal frameworks shows how it ambiguously navigated between authentic and engineered trajectories of involving its target audiences. The creators' anarchist plea for radical change wasambivalently met with appreciation of an urban art space for serious contemplation as well as a perceived lack of local community investment Ð the latter rendering Dismaland an urban Ôart colonyÕ that fostered an elitist global art market rather than urban-citizen-led participation. The in-depth case study concludes that greater attention, both in urban policy and scholarship, is needed to the implications of the production of temporary urban art spaces for immediate inclusive engagement with