Wilson Harris once memorably described C.L.R. James as ‘a great West Indian of complex spirit … a unique Marxist thinker whose dialectic is attuned … to necessity for individual originality as much as it is involved in analyses of historical processes in the life of the people or the body-politic’ (Harris 1986: 230). It is this mode of seeing James that animates this chapter on his contribution to Caribbean literary history. The vastness of his contribution spans seven decades. It commences with the birth of a self-conscious, perpetuating Caribbean literary tradition in the 1920s and ends with an avuncular, deeply appreciative and political significant embrace of the work of African-American women novelists Toni Morrison, Ntozake Shange and Alice Walker in the 1980s, a range that arguably makes him one of the most important Caribbean literary-aesthetic theorists of the twentieth century. However, it is also true that, as dazzling as his work may have been, James, as Aldon Nielsen perceptively argues, ‘never worked out a final literary aesthetics, and to judge from his occasionally contradictory remarks about Melville, Whitman, Sartre, and others, he was till the end of his days very much still in motion from his starting point in literary realism toward an aesthetics that could encompass the formal revolutions of a Wilson Harris’ (Nielsen 1997: xxv).