While Beckett, with his aesthetics of ignorance and impotence, has often been claimed as an antihumanist, his abiding artistic concern remained the elusive question of the human and its ends or purposes. Admittedly, this humanism is “cruelly humane,” as it compulsively excavates the depths of human abjection, suffering and infirmity; but even as the human remains unknowable in Beckett, the impetus to “go on” with the endeavor is appallingly resilient and affecting — and, artistically, it is remarkably fruitful. What emerges from this inexhaustible drive for ends and purposes, in a world of “finality without end” or “purpose without purposiveness,” is a kind of play, which ranges from the laughable and pitiful to the excruciating and poignant. And it is precisely in this play, I argue, that Beckettian humanism and Beckettian aesthetics converge. Revising the aesthetic tradition of Kant and Schiller, his work rejects the beautiful, and its putative harmonization of the mental faculties, as the privileged and proper domain of art; instead, it activates a confrontational aesthetic, the experience of which is predominantly one of discord and discomfort. Through its play, this aesthetic takes us back to our human finitude, revealing, in place of freedom and transcendence, the indefinite and grimly humorous. For Beckett, then, play seems to be constitutive of both the art and the human, and we are never more human than when we play. The ends and meaning will remain indefinite, but such play may have the capacity to revitalize the imagination and encourage us to go on, wherever that may be.