This dissertation explores how Greek and Roman authors use board games and games of chance to answer complex questions about humanity and the relation of the self to the cosmos. I isolate literary topoi rooted in gaming imagery and survey them across a broad diachronic and generic expanse to reveal the application of ludic themes as an important conceptual tool. Specifically, I demonstrate how authors employ gaming imagery to engage in ongoing discussions about the nature of the universe and human behavior; I trace these ludic themes in passages often overlooked as mere metaphor and shape them into an analytical framework that spans major genres from the 8th century BCE to the early 1st century CE.

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