Canto XXIII marks a tragicomic turning point in the Orlando Furioso, as the tension sustaining the titular character’s epic stoicism and romantic chivalry falls away to reveal a maniacal anti-hero. This canto’s staging of Orlando’s madness signals a significant extra-textual literary transition, unsettling the binary of medieval and classical literary traditions that Ariosto draws on, and suggesting a novel genre of literary expression. This article explores one avenue by which Ariosto disrupts such ostensible polarities through the dynamic intertextual practice of writing and rewriting the “Orient.”  A close reading of Canto XXVIII’s resounding echoes of the Thousand and One Nights’ and the lesser-known Hundred and One Nights’ frame tales, illuminates the Furioso’s double focus upon movement toward and away from Muslim-Arab cultural affiliation, a push-pull that opens a space of difference where literary traditions can converge neither in reconciliation nor domination of one another. In particular, this paper examines how Ariosto’s poem captures the ambiguous hybridity of the medieval Mediterranean as an ever-shifting terrain defined not only by oppositionality and hostility, but also by curiosity, exchange, and alliance.