During the classical period in Greece, the immense poetic and cultural authority of Homer came to rest on two central poems, the Iliad and the Odyssey, which differ substantially from each other. While these epics are consistent in terms of language and meter, they contrast sharply in their themes and protagonists. The Iliad is a story of war, while the Odyssey tells the complicated journey of homecoming; Achilles is defined by his βίη, “physical strength,” while Odysseus is remarkable for his μῆτις, “intellectual cunning.” These are only the clearest differences between the two epics, and, as this dissertation shows, many more emerge in the works of Classical and Hellenistic poets, who build on the way that these epics present the same characters and issues from different perspectives. The tragedians and Apollonius composed works that invited comparison with Homer through an overlap of characters or the shared genre of heroic epic, and I argue that these later poets create and respond to a Homeric corpus defined by the differences between the Iliad and the Odyssey. As a result, this dissertation outlines the early iterations of what came to be an enduring strategy in crafting Homeric allusions. For Aeschylus, the Iliad and the Odyssey were still being established as the most prominent works of Homer, and Chapter 1 suggests that his two fragmentary tetralogies based on each Homeric epic play a role in singling these epics out and elevating them for special engagement within tragedy. Chapter 2, on Sophocles’ Ajax and Philoctetes, and Chapter 3, on Euripides’ Trojan Women and Helen, both consider how these plays allude to the Iliad and the Odyssey in contrasting ways as they depict events in the gap between the two Homeric epics. Chapter 4 shifts in time and genre to the Argonautica, which intertwines the plot of its Odyssean voyage with allusions to important Iliadic scenes. Tragedy and Apollonius’ epic thus converge in exploiting the differences between the Iliad and the Odyssey to open up new directions for Homeric reception.