This paper examines two aspects of Odysseus' behavior that fundamentally set him apart from the other Greek heroes in the Iliad. Odysseus at Troy superficially appears to share many traits with the other Homeric heroes: he is a prominent participant both in assemblies and in combat, and he takes part in many of the decisive episodes of the narrative. He shares in the kleos ("glory") of the other renowned warriors by association, but closer examination shows that he speaks and behaves in an idiosyncratic, often unconventional, manner, and that many of his words and deeds reflect a stance of ambivalence towards the war and his role in it. Just as his words and deeds are often incongruous, the very role Odysseus performs in the Iliad is an ambiguous one. Often alone, often aloof, Odysseus stands apart from his companions, and does not fully share in either their glory or their sufferings. Two extraordinary traits further distinguish Odysseus in the Iliad: alone of all the Greeks, he does not cry, and against all conventions, he smiles at an enemy in the middle of a particularly gruesome episode.