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The actors of ancient Greek drama always donned masks as a way of being in character with their assumed mythical identities. My chapter explores the symbolism of prosopon—the mask or face—as a basis for thinking about personal identity in a communal context. The Greek etymology of prosopon suggests an experience of standing ‘before the gaze’ of the other. Thus its purpose exceeds that of a surface through which one communicates, as would be the case for the Latin persona. Instead, the mask of Greek drama helps to open a whole visual arena wherein characters experience what it means to be in relation with each other as a way of being seen by each other. The symbolism of the mask can assist us in constructing a philosophy of personal identity, but only so long as we accept that social recognition is a precondition for acquiring an individual understanding of who I am. My study incorporates historical information about Greek masks that preceded dramatic use—e.g., funerary masks, temple masks, and mask sculptures. Also, I observe parallels between the dramatic mask and contemporaneous Greek sculpture. I weave these ritual, cultic, and aesthetic factors into a paradoxical account of the mask. On the one hand, masks allow characters to ‘fit’ meaningfully within a unified, cohesive sphere of phenomena. The actors occupy a mythological space with aesthetically reinforced identities. On the other hand, the mask has a way of reminding us that human beings ultimately do not fit within their surroundings. The sculpted rigidity of the mask disturbs us with its alien, corpselike features. As an ossified visage, the mask serves as a symbol of mortality. As a mythical and provisional image, it serves as a symbol of socially-derived identity—the self made possible by the gaze of the other.