The customary way to create jazz arrangements of the Western classical canon—informally called swingin’-the-classics—adapts the original composition to jazz conventions. Uri Caine (b.1956) has devised an alternative approach, most notably in his work with compositions by Gustav Mahler. He refracts Mahler’s compositions through an eclectic array of musical performance styles while also eschewing the use of traditional jazz structures in favor of stricter adherence to formal ideas in the original score than is usual in a jazz arrangement. These elements and the manner in which Caine incorporates them in his Mahler arrangements closely parallel the practices of a translator who chooses to create a “foreignizing” literary translation. The 19th-century philosopher and translation theorist Friedrich Schleiermacher explained that in a foreignizing translation “the translator leaves the writer alone as much as possible and moves the reader toward the writer.” Foreignizing translations accentuate the otherness of the original work, approximating the foreign text’s form and syntax in the receiving language and using an uncommon, heterogeneous vocabulary. The resulting translations, which challenge readers with their frequent defiance of the conventions of the receiving linguistic culture, create literal, exaggerated readings that better convey authors’ characteristic use of their own languages for a new audience. My study of Caine’s music—which includes a survey of previously unavailable manuscripts and an exploration of selected arrangements using an analytical method designed to address the qualities in music that parallel foreignizing translation-contextualizes Caine’s modifications to Mahler’s compositions to generate intertextual readings that simultaneously highlight the ways that Mahler was innovative within his own tradition.