This project examines the reading of enslaved characters in Greek and Latin Roman era novels. It is not concerned with "what" ancient Romans thought about slavery but it is vitally concerned with "which" ancient Romans thought about individual slavery and "how" they did so. This project reads fictional representations of slavery as "Novels of Ordeal" in which enslaved characters must struggle to show agency by maintaining gendered honor and demonstrating virtue. It addresses this problem by examining mythical, historical, religious, political, and philosophical backgrounds to the novel through the lens of literary theory, comparative slavery, colonial, and gender studies. It fixes the novels within their cultural contexts as products of Roman Africa and the East by identifying near contemporary "real readers". It compares those readers' receptions of the texts with "our" own historically conditioned reception. The effects of the legacy of African American slavery, the long literary history of the "Captivity" genre, psychoanalysis, and post-modern literary theories are examined as powerful influences on current academic reception of the novels. The dissertation concludes that the novels must be read in response to the imperial Roman project of cultural and religious syncretism but also as an integral part of the World Literature of slavery in dialog with African American, Byzantine, Spanish, and Middle Eastern studies.