This dissertation examines the relationship between British and American conceptualizations of the Anglophone Caribbean and the way that Anglophone Caribbean fiction writers and filmmakers tend to represent the region. Central to my project is the process of reexportation, whereby Caribbean artists attain success at home by first achieving renown abroad. I argue that the primary implication of reexportation is that British and American conceptualizations of the Anglophone Caribbean have had a determining effect upon attempts by Anglophone Caribbean fiction writers and filmmakers to represent the region. Chapter I introduces the dissertation. Chapter II, "The 'Double Audience' of Samuel Selvon and The Lonely Londoners," concerns Trinidadian author Samuel Selvon, who—along with George Lamming, Derek Walcott, and V. S. Naipaul—is cited as being among the most important and influential of the West Indian authors who began publishing in the 1950s. Although I consider all of Selvon's ten novels in that chapter, my main concern is The Lonely Londoners (1956), Selvon's best known and perhaps most pivotal and misread novel. Chapter III, "Contrapuntally Re-reading Perry Henzell's The Harder They Come," features a reevaluation of the Jamaican filmmaker's 1972 motion picture, which in many complex ways remains the Caribbean film. Chapter IV, "Pressure and the Caribbean," focuses on Trinidadian filmmaker Horace Ove's Pressure (1975), which I deliberately treat as a Caribbean film although it is still best known as Britain's first feature-length dramatic movie with a "black" director. Vital secondary texts include selected works by Edward Said, Mikhail Bahktin, and Richard Dyer, as well as Kenneth Ramchand, Keith Warner, and D. Elliott Parris. The three existing book-length analyses of Selvon's fiction are the main voices with which the Selvon chapter is in discourse. David Bordwell's work in cinematic narrative theory and Marcia Landy's contribution to the study of British genres are essential to the frameworks through which I read the cinematic primary texts.