This dissertation reads and interprets Beowulf in the historical and intellectual context of Latin learning and elementary education and argues for possible riddling rhetorical strategies and psychomachic allegory in the Old English poem. This project suggests the learned study of Beowulf to function as a complement to studies of medieval apocrypha, legendary materials, traditional diction and formulaic language in the poem. The texts considered include both Old English and Anglo-Latin literature, in addition to late classical works that seem to feature prominently in early Anglo-Saxon curricula. Attention is given to the Old English poems Guðlac and Juliana from the Exeter Book, the Old English texts from the Nowell Codex (Passion of Saint Christopher, Wonders of the East, Letter of Alexander to Aristotle and Judith), as well as the anonymous Blickling Homilies. Anglo-Latin texts that receive thorough treatment include Aldhelm's Carmen de uirginitate, De uirginitate and Enigmata, as well as Enigmata by Tatwine, Eusebius and Boniface, Alcuin's Disputatio Pippini cum Albino and the anonymous Liber monstrorum. This project considers especially the Old English Riddles located in the Exeter Book and suggests that rhetorical strategies featured in Anglo-Saxon riddles (and enigmata) may operate also in Beowulf and constitute an enigmatic design in the poem. After reflecting on an association between riddles and monsters in the Anglo-Saxon riddle tradition, this dissertation reviews the literary influence of the Prudentius' late classical Christian epic, the Psychomachia, in the development psychomachic allegory in Anglo-Saxon literature. This project then analyzes the parallel representations of monstrous vice in both the Psychomachia and Beowulf, and it proposes that Prudentius' allegorical poem may have acted as a model for characterizations of heroism and monstrosity in Beowulf. The dissertation concludes that the Psychomachia may be regarded as an analogue to Beowulf, and that both poems share concerns about warrior ethics within the context of Christian morality.