Cynicism styles itself as the answer to the mental suffering produced by disillusionment, disappointment, and despair. It seeks to avoid them by exposing to ridicule naive idealism or treacherous hope. Modern cynics avoid the vulnerability produced by high ideals, just as their ancient counterparts eschewed dependence on all but the most essential of material needs. The philosophical tradition of the Cynics begins with the Ancients, including Diogenes and Lucian, but has found contemporary valence in the work of cultural theorists such as Peter Sloterdijk. This article uses theories of cynicism to analyze postcolonial disappointment in Irish modernism. It argues that in the “ambi-colonial” conditions of early-twentieth-century Ireland, the metropolitan surety of and suaveness of a cynical attitude is available but precarious. We therefore find a recursive cynicism that often turns upon itself, finding the self-distancing and critical sure-footedness of modern, urbane cynicism a stance that itself should be treated with cynical scepticism. The essay detects this recursive cynicism in a number of literary works of post-independence Ireland, concluding with an extended consideration of W. B. Yeats’s great poem of civilizational precarity, “Nineteen Hundred and Nineteen.”