This dissertation is a study of the interplay of regionalism and globalization in the work of William Faulkner (1897-1962) and Derek Walcott (1930-). Through a survey of contemporary criticism delineating a common “postplantation” region that encompasses both the U.S. South and the Caribbean and an interrogation of the discourse on relationality and “chaotic” literary production by such theorists as Édouard Glissant and Antonio Benítez-Rojo, I conclude that the indicated authors, in their capacity as writers incontrovertibly attached to specific regions (Faulkner’s Yoknapatawpha County and Walcott’s St. Lucia) yet simultaneously belonging to global networks of literary interchange, evince a unique redeployment of regional styles within postmodern currents of locational indeterminacy. My major claims are as follows: firstly, the literary region, rather than being locked in an oppositional relationship with forces of globalization and internationalism, is dialogically linked with those forces; secondly, regionalism, far from forbidding inclusion within a global reading community, is in fact generative of interregional comparability; and thirdly, attempts to destabilize or decentralize the notion of the region in literature are another way of reifying regional distinction. I support these claims through surveys of existing and emerging criticism of these authors’ works and careers, interpretations of seldom-studied early translations of Faulkner’s work into German, and close readings of a selection of novels and poems, most prominently Faulkner’s Absalom, Absalom! (1936), Go Down, Moses (1942), and A Fable (1954), and Walcott’s The Gulf (1969), Omeros (1990), and The Prodigal (2004). In all of these sources, I show, conceptions of these authors’ “home” regions attempt to bring those regions into dialogue with other locales, yet even as these stable regional vantage points proliferate outwards into global space, they simultaneously pull inward, toward a reincarnation of regional particularities. Ultimately, I suggest that the region as manifested in these two authors’ writings is less destroyed or defeated by the decentralizing pressures of the globe than implicated in a mutually constitutive relationship with those pressures.