Examining attitudes towards failure, loss and inadequacy as they appear in Greek literature from the eighth to the fourth century BCE, this book incorporates two major themes: failure in mythological narratives and in historical accounts. These two areas are further divided into narratives of heroic and divine failure and accounts of individual and collective failure. Myth and history are examined under the same lens while mythological narratives are also placed in the historical context of the literary works in which they appear. Greek epic, for example, the cultural product of an honor-shame society, emphasizes success and the attainment of goals achieved in the context of intense trials; without shying away from human or divine deficiencies, epic poetry prefers to glorify the pursuit of personal fulfillment. Analysis of key texts identifies the intertextual discourses that reveal epic attitudes towards failure, such as Agamemnon's inadequacies in the Iliad, Odysseus' shortcomings in the Odyssey, and Peirithoos' catastrophic descent to the underworld. This study also joins narratives from major cycles of Greek myth (the Trojan war, the labors of Hercules, and Athenian foundation myths) with historical accounts of disastrous military campaigns (the Ionian revolt and the Sicilian expedition) to offer a diachronic outlook on failure in Greek antiquity