This dissertation offers the first in-depth study of racial difference, and specifically blackness, in premodern Arabic popular literature. I base my study primarily on the historically orally performed chivalric legend (sīra) about the Arabo-Byzantine wars of the 7th-9th centuries, Sīrat Dhāt al-Himma, and make frequent comparative reference to Sīrat Banī Hilāl, which concerns the Hilāl tribe’s conquest of North Africa, Sīrat ‘Antar, about the adventures of the half-Ethiopian pre-Islamic warrior poet, ‘Antara ibn Shaddād, and other near-contemporary sources. Using these works, the project assesses the portrayal of black heroes in popular lore from the time of their often-miraculous conceptions. This dissertation isolates three main sites of literal and figurative racial construction through which the movement and status of black figures in the sīra’s imagined world are elaborated: the black hero’s birth, his coming of age as a leader and concurrent establishment of a set of military companions, and the contacts that the hero develops with other black cultures both within Africa and in diasporic contexts. Each such vignette incorporates several subgenres, showcasing how “race talk” manifests across different literary forms such as narrative prose and poetry. Because the sīras have long existed between oral and written media, many variations of them exist. I therefore have used several editions of the sīra to explore how racialization can shift and change in subtle ways even in the same work as it moves from context to context. The first chapter of the dissertation offers a primer on blackness in pre-modern Arabic literature, in which I elaborate a set of reading practices and theories through close attention to manifestations of blackness in a selection of exemplary texts, namely the Qur’ān, the 9th-century litterateur al-Jāḥiẓ’s epistle Fakhr al-Sūdān ‘alā-l-Bīḍān (“The Boasting of the Blacks Over the Whites”), ‘Abbasid-era muḥdath (avant-garde) poets who dealt with black subjects, and the 1001 Nights. In the second chapter, I examine the birth narratives of black heroes found in the early sīras, two of whom are born non-hereditarily black to Arab parents. I find that in these texts, scientific discourses come to the fore; the heroes’ existences are explained mainly through biological accident, demonstrating that scientific precepts have long been a common way—among both high and popular culture—of reasoning through human differences. The heroes’ epidermal blackness and genealogical Arabness confers an ideal balance of the traits commonly associated with the two cultures, rendering them ideal, hybrid heroes. As such, the third chapter examines how the hero’s Black-Arab hybridity serves as a means of negotiating between the Arab and African groups who comprise the Muslim armies in Sīrat Dhāt al-Himma. The main hero in the text often engages in relationships of clientage and fosterage with his black peers, drawing them into Arab tribal affinities. I thus propose we can read the central black hero as a medium for the assimilation of other black characters in the text. This reflects an aspect of the spread of Islam that is visible across other near-contemporary literary forms, especially prosopographic works, through which non-Arab converts could have their lineages rewritten so as to be traceable to Arab or prophetic heritages. The fourth chapter evaluates representations of non-Muslim blacks in the text by looking at the portion of the sīra that takes place in Abyssinia, and considers in particular the question of how race “travels” between Arabia and Africa; the text demonstrates ample awareness of race as something situational rather than fixed, leading to a complex understanding of racial affinity and animus that transcends the anti-black racism expressed elsewhere. This dissertation shows that pre-modern racial thinking is neither innocuous nor flatly racist, but rather complex and variegated even within a single literary unit. It finds that there were several theories explaining how racial difference occurred biologically, which were used in the sīras to heighten tensions, stage Black-Arab relationships, and engender heroes who were simultaneously from prominent lineages and were ethnically disadvantaged, resulting in characters of wide appeal and utility. It also expounds on the dynamics of continuity and evolution between pre-modern and modern racial logic in the Arabo-Muslim world, particularly via both scriptural interpretations and the Classical inheritance of Greco-Roman medical and philosophical works that are common to several cultures.