Black radical artist Sun Ra’s relationship with jazz’s histories was materially and sensually different from that of his contemporaries in the Afrological musical avant-garde. He adopted an exaggerated and playful—yet lovingly attentive—mode of engagement with his predecessors, notably bandleader-pianists Fletcher Henderson and Duke Ellington, that could be read as an ongoing series of drag interpretations. This chapter examines one of Sun Ra’s live recordings of “Queer Notions,” a composition by swing-era saxophonist Coleman Hawkins, arranged by Henderson, that in its time was already queering aspects of jazz syntax. This analytic foray is in the service of larger rumination on the relation between music analysis, the lives and actions of musicians, and both real and “fabulated” histories. In doing so it draws largely on the work of Jose Esteban Muñoz and others, considering how what has been richly theorized as “queer temporality” can be put to work in musical inquiry.