This article compares how two contemporaneous Anglophone Caribbean writers – Trinidadian V.S. Naipaul (1932–2018) and St. Lucian Derek Walcott (1930–2017) – explore the challenges posed to ontological security and nationhood in the Caribbean by considering how myth (broadly interpreted), knowledge, and ignorance of Caribbean history interact in understandings of their respective islands. The article focuses on one work by each – Naipaul’s The Loss of El Dorado and Walcott’s Omeros – which mediate myth and history through artistic discourse in a similar way. Hitherto the personal and literary differences between Naipaul and Walcott have been stressed by their critics more than their similarities; this article points towards the latter. Both writers are aware of how the presences and absences of Caribbean history can give rise to the mythologization of both Caribbean and foreign nations. They condemn the emotional and moral simplicities which both imperial and anti‐imperial mythologizing involve. Yet both of them write works which perform as well as condemn such mythologization with regard to their own islands. Whilst not rejecting a careful handling of documentary sources, both writers are aware that recreations of history inevitably involve imagination and desire, and as creative writers they embrace this premise.