The literary remains of three Roman freedpersons--the editor and biographer Tiro (c. 80-4 BCE), the poet and fabulist Phaedrus (fl. 1st cen. CE), and the philosopher Epictetus (c. 55-135 CE)--give us a rare glimpse into the internal experience of persons enslaved and emancipated by Roman elites. To contextualize these experiences, we study the legal basis of Roman slavery, epigraphic self-representations, and stereotyping representations of freedpersons by free authors. We also read our authors against comparable works by freeborn analogues--the senator Cicero, the poet Horace, and the philosopher Seneca--to test the boundaries of how the identity of libertus ("freedman") affected and failed to affect our authors' literary aims. To deepen our study of how historical conditions shape the creation of freed authorship and the transmission of freed authors, we also read, and consider the conditions surrounding the publication of, American freedpersons' literature.