Elia Levita, grammarian, teacher of Hebrew to many Christian humanists in the first half of the Sixteenth century, is also the author of two Yiddish epic romances inspired by Italian sources, Bovo‐Buch and Paris un Wiene, which are considered to be among the finest works of old Yiddish literature. These romances relating love‐stories between knights and princesses reveal a precise knowledge of contemporary Italian culture, particularly the tradition of romanzo cavalleresco. Bovo‐Buch, composed in 1507, has left a significant mark on the whole history of Yiddish culture. It is characterized by its freedom of tone and popular expressive style. Paris un Wiene, probably written in the 1530s, owes much to Ariosto’s Orlando Furioso. At the same time, it shows a mastership in the art of satire which might originate from a long tradition of Hebrew poetry. This article aims to present the rich cross‐cultural influences which lead to the composition of Elia Levita’s two Yiddish masterpieces.