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Although slavery was a widely accepted practice throughout the ancient Mediterranean, the Roman system was distinctive for its high rates of manumission and grant of citizenship to slaves manumitted through official channels. This dissertation sheds new light on the role of ex-slaves in Roman society by examining the cultural exchange that took place between members of this population and the ruling orders. Rather than reproduce ancient stereotypes, on the one hand, or idealize the level of agency that freedmen enjoyed, on the other, I focus on the dialogue between status groups and on the media through which that conversation occurred. Particular attention is given to the interaction between literary and epigraphical writing. I argue that during the early Empire, when elite values were being reconfigured to accommodate the rise of monarchy, freed slaves offered constructive models of behavior even as they were subject to intense social prejudice. Inscriptions are our best source of evidence for the beliefs and practices of Roman freedmen, and I analyze these texts alongside the literary sources to show how the virtues of deference and industry wer