There have been numerous studies of the transmission of literatures of the medieval Arab world to al-Andalus, such as those by López-Baralt and Menocal. There have also been various studies examining the transmission of literatures from Golden Age Spain and Portugal to Latin America, such as Roberto González Echevarría’s Celestina’s Brood. There have, however, been almost no studies that examine continuities between the literatures and cultures of the medieval Arab world and modern Latin America through al-Andalus. Utilizing existing scholarship and an approach derived from romance philology, this study examines the continuities between the shadow plays of Iraqi poet Ibn Daniyal, written and presented in Cairo around 1300, especially The Shadow Spirit, which features a sexual go-between, and Celestina, by Fernando de Rojas, published in Salamanca in 1499. The study then looks at the intertextual links between Celestina and the Cuban Severo Sarduy’s postmodern novel Cobra, published in 1972, which also has a sexual go-between as a principal character, and the substantial affinities Cobra shares with The Shadow Spirit. The study suggests that these texts, and many others, can fruitfully be viewed as belonging to a centuries-long translinguistic tradition that includes works from the Arab world, the Iberian Peninsula, and Latin America.