This dissertation investigates the life, writings, and reception of Marcus Tullius Tiro, a Roman freedman who had formerly been enslaved to Cicero. Its five chapters employ literary and historical approaches to analyze extant sources and to discern what they are able to tell us about Tiro. Chapter one offers a literary reading of Ad familiares 16 that demonstrates how this book of letters tells a story of Tiro’s rise from enslavement to becoming a successful Roman citizen. This analysis of Ad familiares 16 suggests that its letters present a curated portrait of Tiro, which may skew the reliability of this book as a straightforward historical source. Chapter two therefore turns to comparative evidence, particularly Epistulae ad Atticum, in order to establish a clearer understanding of the labor and status of Tiro, as well as other enslaved and freed people connected with Cicero’s household. Chapter three then moves beyond Ciceronian sources in order to study Tiro as an author and scholar in his own right. By analyzing fragments and testimonia of Tiro’s writings, the chapter contextualizes Tiro’s work in the intellectual culture of the first century BCE and suggests how Tiro used authorship as a means of self-fashioning. The final two chapters of the dissertation investigate Tiro’s afterlives in antiquity and in later historical periods. Chapter four provides a detailed analysis of Tiro’s reception in the writings of ancient authors, showing how Tiro became a symbolic figure in the classical tradition. Chapter five then presents case studies that explore Tiro’s afterlives in a selection of sources from the fourteenth to the twenty-first centuries. Taken together, these five chapters construct a multifaceted account of Tiro and his legacy.