Jamaican fiction published in the 1960s was fundamentally pessimistic. These writings drew from regional ontologies of religious millenarianism, colonial abjection, and racial damnation, as well as of existentialist philosophies of Albert Camus and Jean-Paul Sartre, to offer representations of pessimisms that embraced life's absurd futility rather than its abject hopelessness. Reading the corpus of this Jamaican literary archive—twelve novels and one memoir—the author examines the heterogeneous nature of the decade's literary pessimisms, best characterized as a sensibility of radical skepticism, which approached the absurdity of the current conjuncture by deploying critical distance to cast doubt on the past, the present, and the very idea of single-island sovereign futures. The author resituates this independence era's literature by identifying its multitudinous plotlines that included resentment, betrayal, disillusion, disappointment, detachment, shame, and contempt. Thus, rather than understanding pessimism as debilitating impasse or frustrated returns, thinking through its generativity reveals how these late-colonial-Jamaican writers anticipated current critical theories about failure's productivity. Radical skepticisms, the essay argues, create conceptual ground to accommodate the multiple political and affective responses in, and to, the independence era.