This paper explores the ways in which the qiyan—highly trained female singers held as by the courtly elite in ‘Abbasid Baghdad and Umayyad Andalusia—were represented and depicted in medieval literary and historical narratives. More specifically, I examine how medieval authors used depictions of the qiyan as rhetorical strategies for advancing the broader political and philosophical agendas that their texts were intended to address. Because the qiyan did not write their own biographies, our understanding of these singing slave women cannot be separated from the broader literary, political, philosophical, and theological agendas of the texts in which they are discussed. In light of this reality, my paper does not attempt to reconstruct the experiences of the qiyan themselves. Rather, I attempt to return the qiyan to their original context by considering how the subject of the qiyan was mobilized for specific narrative purposes by medieval authors. This paper suggests that the subject of the qiyan was a literary motif loaded with significance and coded meanings, used in ‘Abbasid and Andalusian historiography to convey specific ideas about court culture, imperial splendor, and refinement. This motif, in turn, was imbricated with ideologies about gender dynamics, power relationships, historical memory, and the articulation of Muslim identity and imperial legitimacy.