The paper is focused on the adaptation of the image of Cerberus in Russian culture of the Middle Ages and the Early Modern Times. Fragmentary information about some characters of the Greco-Roman mythology penetrated into Russian medieval literature from the Byzantine. Christians often borrowed and reinterpreted those images in the traditions of Christian symbolism. One of these characters, Cerberus, the dog of Hades, became an infernal character: a guard or a demon of the Christian Hell. As a dog it turned into an Evil animal, executioner of sinners. Аs a three-headed creature it resembled dragons and other legendary monsters. Perhaps, the story about Hercules, who tamed Cerberus, became the basis of novel in the Sinai Patericon (story about Saint John Kolobos and graveyard hyena). At the beginning of the 18th century Russia experienced a secondary influence of Ancient symbolism through Western European emblematic collections and similar translated works. A lot of exotic images were rediscovered and aquired new meanings. Under the influence of the Jesuit theatre, the mouth of Cerberus became a variation of a well-known in Russia iconographic image of Hellmouth. In the plays by Dimitri of Rostov, the characters sent to the underworld found themselves in the mouth of a monstrous dog – inside an ingenious stage device. Toward the end of the 18th century Hell as a dog’s head appeared also in Russian popular prints, lubok.