The borderline between philosophy and literature is highly contested. Still, if literary theorists and philosophers agree on the occasional work’s ability to transcend border norms altogether, Samuel Beckett’s Endgame is a piece of dramatic writing that amply deserves the distinction. My article attempts a symptomatic comparison between the existential condition of Endgame’s characters, on the one hand, and the philosophical predicament, on the other. The importance of failure – both as an obstacle and as a catalyst for regeneration – provides (...) a useful framework for this cross-disciplinary comparison. I draw inspiration from Stanley Cavell’s reading of Endgame, but I take Cavell’s analysis a step further. In ‘Ending the Waiting Game’ Cavell finds satisfaction in discovering what Beckett’s play can say about a specific school of philosophy – logical positivism. I treat this discovery as an invitation to consider the possibility of a broader conclusion. There is much in Endgame, in Cavell’s other writings, in the works of his and Beckett’s commentators and in Wittgenstein’s legacy that points to the existence and acceptance of philosophical infirmity. I see the recognition of this infirmity as a necessary step towards a better understanding of the play but also as a contribution to our general sense of the productive continuities between philosophy and literature. (shrink)