The political struggles that delivered the first wave of independent Caribbean nation states are often retrospectively characterised under the banner of nationalism, but it is important to acknowledge the diversity of ideologies and affiliations that were involved in the transition towards non-colonial sovereignty. This chapter explores the role that writers and imaginative writings played in shaping alternative political imaginaries in the Anglophone Caribbean region from the 1920s to the 1960s. Its arguments expand the terrain of literary nationalisms beyond the now canonical fictions of male Windrush generation novelists writing at the mid-century. It attends to the nascent nationalism invoked by literary projects at the turn of the century, considers the role assigned to the writer in the short-lived project of Anglophone regional Federation between 1958 and 1962 that predated the constitution of nation states, and explores how Pan-African and Black Atlantic movements powerfully shaped the decolonial literary imagination in the early twentieth century. It also acknowledges the crucial role that women played in male-centred histories and politically engaged literary traditions.