This chapter approaches questions of social aesthetics through a narrow focus on Billy Strayhorn’s work as a vocal arranger. Strayhorn’s work with singers merged the musical and personal in particularly gendered ways. Barg theorizes the gendered musical and personal terrain of his collaborations both for the paths of musical meaning toward which it might direct us and for how they mark what the historian Matthew Tinkcom has called, in a different but related context, the “queer labor” of gay male artists working behind the scenes in the entertainment industry. Strayhorn’s musical legacy presents an intriguing and distinctly queer paradox: he was a very active musical presence, and his compositions and arrangements were enormously influential, yet he remained largely anonymous in the public sphere. Strayhorn’s dissident sexual identity required that he work in the shadow of a collaborator, a distanced but empathetic space from which his voice could merge with and give shape to the voices of others. How, then, might we relate the queer conditions under which Strayhorn labored to his aesthetic practices as a vocal arranger and to the gendered labor and position of the singers with whom he worked?