The elite core of musicians in both the Umayyad and Abbasid courts consisted of a constantly changing roster of free, unfree, foreign and client artists. Due to the flexibility of musical and social terminology, it is difficult to specify the degrees of difference, but regardless of origin or legal status, all court musicians had access to social mobility. While having musical talent was fundamental, it was only one of several skills necessary to earn patronage. Sources as varied al-Isbahani’s Kitab al-Aghani, Ibn al-Washsha’s Kitab al-Muwashsha and the anti-sama? treatise Response to a Question Regarding Music by al-Adjurri suggest musicianship incorporated a complex array of technical skill, genre choice, and gender identity, all of which influenced reception of musical performance. Despite the importance of music at court, performing musicians existed on the margins of society. Their liminal status was linked to the perception of performers as mere technicians, as well as shifting perceptions about the moral and social acceptance of music. Yet, their marginality also gave musicians the ability to slip between physical and social borders. Representations of the performance of qiy?n and mukhannath?n best demonstrate this ability, as these roles visibly incorporated gender into their music identity. As members of both the women’s quarters and musician ranks, qiy?n were never fully contained by physical or social boundaries. Qiy?n could dress and wear their hair as boys (as with the fad for ghulamiyyat), or enhance their femininity by writing poetry on their bodies. Likewise, mukhannath?n, who adopted feminine dress and gesture, had access to male and female spaces through their patrons. Though gender play was frequently intertwined with sexuality, some gender performance seems to have been used to satirize or manipulate social convention for individual advancement. Therefore, qiy?n and mukhannath?n, I suggest, used their music and gender performances as a mode of agency. In this paper, I explore the relationship between gender and music performance of qiy?n and mukhannath?n as represented in select 9th and 10th century texts. My primary questions are: How important was gender identity to musical performance practice and reception? Why did some musicians incorporate gender play into their performance and others not? Lastly, how did their performance impact the reception of music overall? To place these intersections of gender and musicianship within a wider context, I conclude with a brief comparison to select medieval cultures with similar musical figures.