This Element revisits the relation between Giacomo Leopardi and Samuel Beckett to argue that the dialogue between them might offer new ways of thinking about the nature of both writers' pessimism. The authors suggest that Leopardi becomes increasingly important for Beckett, not only because he frames a literary philosophy of scepticism, but because he gives a rich account of the means by which thoroughgoing pessimism might open on to an unenchanted mode of persistence. In doing so, the Element looks past the impasse - between going on and not going on - that threatens to forestall imaginative possibilities for both writers.