Our paper adopts a paradoxical mode of analysis in order to reconstruct the inherently paradoxical constitution and conceptualisation of work as function and/or meaning in itself. The effects of this dichotomisation of work also underlie the current debate on so-called social and artistic critiques of capitalism, to echo Boltanski and Chiapello’s distinction in The New Spirit of Capitalism, and the diagnosis of how artistic practices and claims are subsumed under the logic of capitalist organization. It is here that we situate the thesis of play’s incorporation into capitalist development. Unfolding an understanding of work that acknowledges and keeps open the play of paradoxes that produces ‘work’, we problematize the diagnosis of the unavoidable incorporation of play. The insolubility of paradox and the paradoxical constitution of work reopen rather than foreclose the question of play and thus the possibilities and capacities of artistic critique.