I argue that Nietzsche’s criticism of the Kantian theory of disinterested pleasure in beauty reflects his own commitment to claims that closely resemble certain Kantian aesthetic principles, specifically as reinterpreted by Schiller. I show that Schiller takes the experience of beauty to be disinterested both (1) insofar as it involves impassioned ‘play’ rather than desire-driven ‘work’, and (2) insofar as it involves rational-sensuous (‘aesthetic’) play rather than mere physical play. In figures like Nietzsche, Schiller’s generic notion of play—which is itself influenced by Kant’s claim that aesthetic pleasure is orthogonal to desire-satisfaction—becomes decoupled from his (further) Kantian view that aesthetic play essentially involves a harmony of sensuous receptivity and rational spontaneity. The result, I suggest, is a self-standing opposition between desires and passions. This motivates a recognizably Romantic vision of aesthetic disinterestedness, as freedom from desire realized in a state of creative determination by passion.