Beginning around the mid-1930s, clarinetist and bandleader Benny Goodman engaged with classical music, adding standard solo pieces to his regular performance and record portfolio. He also stimulated the emergence of a modern clarinet repertoire by granting commissions to composers, such as Béla Bartók, Paul Hindemith, Darius Milhaud, and others. In this article, I explore why and how these projects evolved and how the collaborations unfolded. My focus is on the commissions to Hindemith (1941/47) and Milhaud (1941). The newly found correspondence of Eric Simon, a Viennese-born clarinetist who advised Goodman and initiated contact with Hindemith and Milhaud, reveal Goodman's “double life” as a multilayered sphere for various actors, each with their own specific background and agenda. My analysis follows three topics that decisively shaped the investigated projects: Goodman's relationship with classical music, which I discuss in light of the intersectionally biased structures of U.S. musical life; the situation of European émigré artists experienced by Hindemith, Milhaud, and Simon; and the promotion of new music, which linked the lives, networks, and agendas of the aforementioned protagonists and even defined their relationships. By highlighting Goodman taking center stage as a performer-commissioner, I argue for more serious attention to performers’ impact on musical production and repertoire formation, given that they represent the ultimate gatekeepers to the living repertoire.