This article offers an explorative reading of a parodic Yiddish rendition of T.S. Eliot’s “The Love Song of J. Alfred Prufrock” entitled “Der shir hashirim fun Mendl Pumshtok” that was composed by Isaac Rosenfeld and Saul Bellow during their student years in Chicago. The article argues that, by measuring themselves against the main representative of high modernism and by giving a markedly ethnic inflection to Eliot’s poem, Brooks and Rosenfeld attempted to transcend the assumed provincialism of their situation and elbow their way into the American literary canon. More generally, the article suggests that parodic “translations” of this kind, by highlighting the postvernacular dimension of literary language (Shandler), extend the purview of translingual studies by valuing performativity, orality, and collaboration over and against competency as defining elements of linguistic border crossing in an age that has sometimes too hastily been characterized as post-national or post-Romantic. The article thus points to the relevance of what the author calls literary amphilingualism, a prevalent but understudied phenomenon in translingual studies.