Working outward from Edward Kamau Brathwaite’s landmark 1974 essay, “The African Presence in Caribbean Literature,” this article explores the fuller history of the idea of Africa in anglophone Caribbean critical and literary works from the 1930s to the 2000s. It demonstrates that earlier, now forgotten Caribbean critics drew on imperfect and incomplete Caribbean literary imaginings of Africa to frame a counter-colonial politics of identity. The essay also brings back into view writings by Una Marson, Victor Stafford Reid, and Derek Walcott that expressed a different politics of solidarity based on the shared experience of colonial violence. Readings of recent literary works by Charlotte Williams and Nalo Hopkinson reveal the contemporary crafting of this relation around a heightened awareness of both presence and loss, history and imagination. Importantly, this gathering of sources and perspectives allows for an appreciation of the role that a reach toward Africa has played in articulations of Caribbeanness and its complex patterning of cultural co-belonging.