This chapter examines the vision of key non-fictional essays written by creative writers such as C. L .R. James, Wilson Harris, George Lamming, Salman Rushdie, etc. and puts them in dialogue with the critical and theoretical debates of major literary and cultural critics such as Stuart Hall, Paul Gilroy, Homi K. Bhabha, Avtar Brah, and others. Pointing to shared areas of concern, elements of synergy, and extracting elements which illuminate the historiography of creative and critical exchange, this chapter focuses on particular moments of cultural intervention. It traces how the history and development of this body of writing – which has now gained belated acknowledgement – as well as the literary, cultural, and theoretical debates that have surrounded it are inextricably linked with its political and historical context of emergence.