This paper contributes to a growing field of interest in urban futures through an examination of modes of play, pleasure and participation in urban life that pose challenges to a prevailing techno-utopian imaginary. My analysis centres on an archival study of the experimental urbanisms advanced by the British theatre director Joan Littlewood, who from the early 1960s onwards, increasingly rejected formal theatre in favour of approaching the city itself as theatre. Conceived within her pioneering Fun Palace project, I argue that Littlewood’s elucidation of the city as theatre was significant for the ways it intervened in the spaces and subjectivities of everyday life while articulating possibilities for a radically more ‘delightful’ urban future. In particular, I trace how Littlewood’s approach sought to transform the lives of the urban working-classes, using performative understandings of play and pleasure to repurpose the social, cultural and technological advances of the era for their own ends. This examination is developed through Littlewood’s archetypal figuration of the clown, a character that she variously deployed to signal alternative forms of urban expertise, and to animate the potential for new modes of playful and pleasurable urban inhabitation. My central argument therefore contends that Littlewood’s city of theatre, and her generative evocation of clowning, provide both an incisive critique of, and prescient alternative to, dominant techno-utopian visions of the future city. Ultimately Littlewood is repositioned here as an overlooked urbanist whose influential theatrical ideas serve to enrich geographical understandings of the urban future in ways that remain relevant today.