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Odysseus's caution to avoid comparison with prior generations at the beginning of the Phaeacian episode (Od. 8.223-25) is consistent with his self-positioning against Heracles at the end of the Nekyia. As I argue, the encounter between Odysseus and Heracles needs to be read in conjunction with Odysseus's attitude towards older generations of heroes and with the abrupt and fearful exit of Odysseus from the Underworld. This paper discusses the end of the Nekyia in light of the tradition of the Gorgon and re-examines the dynamics of Odysseus's puzzling encounter with Heracles.