The central concern of this paper is to explore the efforts of Schiller's post-Kantian idealism and Marcuse's critical theory to develop a new conception of free human experience. That conception is built on the notion of play. Play is said to combine the human capacities for physical pleasure and reason, capacities which the modern world has dualized. Analysis of their respective accounts of play reveals its ambivalent form in the work of both philosophers. Play supports the ideal of ‘freedom from (...) necessity’, understood as a release from all external constraint. But it also appears to serve as a model for ‘freedom as a higher necessity’. In the case of Schiller, the ambivalence encompasses idle play and an obligation to make ourselves worthy of freedom. For Marcuse, play represents a kind of libidinal idleness while also underpinning a non-alienated conception of labour. (shrink)