Starting from the concept of a “play-drive” as introduced by Friedrich Schiller in his Letters on Aesthetic Education, the present study explores this concept at the interface of the crossroads between philosophy, anthropology, and aesthetics. In order to grasp what may be called the “space” of these phenomena, reflection must engage the relationship between Ancients and Moderns as well, to show that the figure of “the child” in Nietzsche and Heraclitus is apt to give its full dimension to Schiller’s theory of “play” as the consummation of humanity.