This article examines the turn to the aesthetic dimension in early 20th century critical theory, particularly in the work of Lukács, Benjamin and Adorno. It focuses on the concept of play ( Spiel), which garnered particular attention as a possible form of aesthetic resistance to the reification of reason in modern society. The article traces the concept of play from the work of Lukács, who engaged with Schiller’s notion of the play-drive but ultimately viewed it to be an inadequate form (...) of aesthetic resistance, to the work of Benjamin, who optimistically embraced the revolutionary possibility of play. In contrast, the article argues that Adorno’s work tacitly advances a critical concept of dark play that offers a third perspective between Lukács’s pessimism and Benjamin’s optimism, thus avoiding both the retreat into an apolitical aesthetic dimension and the uncritical embrace of play’s revolutionary potential. (shrink)