Homer's portrayal of Achilles and Odysseus in the Iliad and the Odyssey as opposite character types had an enormous influence on subsequent literary and critical discourse. Two extraordinarily rich contexts of reception between about 475 to 350 BC were Athenian dramatic and philosophical literature. These two genres share an overriding concern with the suitability of one or the other of these characters as models for ethical behavior in contemporary political and social circumstances. This complex process of reception was repeated between about 240 and 50 BC when Roman playwrights and intellectuals faced similar Homeric challenges in adapting Athenian meditations on these problems to the Roman stage and to the creation of a philosophical literature in Latin. My project traces this strand of literary and philosophical history as part of the background to the continuing influence of Homer on other literary genres, principally epic poetry, in Alexandria and in Rome.