George Lyman Kittredge was professor of English Literature at Harvard and one of the most influential literary critics of the early 20th century. He is best known for his edition of the works of Shakespeare, but wrote on the Canterbury tales and other works of Middle English literature. In this paper he examines the medieval romance of Sir Orfeo against its classical predecessor in Ovid's Metamorphoses. This paper offers to the students of Classics and Medieval Studies the opportunity to read a work of multidisciplinary literary criticism by one of the greatest minds in the field.