Introduction. The article critically examines the epitaph of George Akropolites on the death of Emperor Johannes III Ducas Vatatzes. The Epitaph of George Akropolites is a remarkable example of Byzantine rhetoric. The highly educated Byzantine author, proud of his splendid education and skillful rhetorician, fully expressed in this work his knowledge of ancient topics and biblical aesthetics. Methods and materials. The article is written in the context of hermeneutic methodology. We assume that the epitaph of George Akropolites requires a deeper interpretation, which will help to reveal the implicit meanings hidden in the text of George Akropolites. Analysis. First, in the epitaph of George Akropolites, Charon is synonymous with death. This is not an ancient reminiscence, as it may seem, but a popular character of the Acritic folklore of the 9th – 11th centuries, popular among the military class. Akropolites would soon become acquainted with this class, becoming praetor in 1256, when he would be extremely unsuccessful in commanding an army in western Macedonia. Secondly, it is worthwhile to look closely, following K. Praechter, at the expression of George Akropolites “the emperor became the paranáloma of Charon”. In our opinion, paranáloma is an extremely interesting word that takes us into the archaic and chthonic world and presents George Akropolites as a remarkable connoisseur of a wide variety of philosophical and medical texts, particularly the Neoplatonic writings of John Philoponus (c. 480–570) and Simplicianus of Cilicia (c. 490–560). Results. In summary, we have before us a whole literary tradition revolving around a natural-philosophical reading of the folkloric underworld and Charon, which gives for George Akropolites a large stock of metaphors and an opportunity to show his education.