By the end of the twentieth century, trailblazing novelists such as W. Adolphe Roberts, Roger Mais, John Hearne, V. S. Reid, and Garth St Omer, were out of print, and their immense contribution to the Caribbean literary landscape obscured. The reasons for the short-lived popularity of these Caribbean novelists range from the interplay of race; the compass of the thematic reach of their novels; the radically evolving sociopolitical landscape within which these writers were being read; and international dynamics of critical reception. The mapping out of these trajectories of oblivion also reveals a fascinating network of alliances, affiliations, and geo-locations that is core to the literary history of the Caribbean. The chapter, in showcasing the current reprinting efforts of these aforementioned novelists by publishing houses such as Peepal Tree Press and the University of the West Indies Press, argues that academicians can also play a role in this literary comeback. In engaging with the relevance of these restored novelists to contemporary critical contexts, teachers and critics can help locate the reprinted texts within the complicated and intricate dynamics of Caribbean society, ongoing literary debates, and the tradition of homage Caribbean writers paid and continue to pay to each other.