In this study of David Foster Wallace’s Infinite Jest, I combine the linguistic and literary theories of renowned scholar Mikhail Bakhtin to create a new lens through which to consider Wallace’s thematic project. Combining Bakhtin’s linguistic theories of dialogic conflict and heteroglossia with his literary theories on the grotesque provides an integrated stylistic methodology that illustrates the connections between Wallace’s use of imagery and style. In view of his use of both grotesque liminal imagery and dialogized heteroglossia, Wallace’s seemingly obsessive use of language is recast as a manifestation of grotesque embodiment that reflects the postmodern mileau in which he writes. I propose that Wallace crafts a series of grotesque stylistic devices that shape his words to match his theme. I propose two particular grotesque stylistic devices: narrative bleed in which the seemingly neutral narrative voice begins to reflect particular character discourses and character-to-character voice bleed in which dialogic conflict between characters is dramatically rendered within the novel.