This article examines and contextualizes Arnold Schoenberg’s arrangements of waltzes by Johann Strauss, arguing that they demonstrate how Schoenberg’s music, while radically modern, was at the same time profoundly shaped by nostalgia. This particular type of nostalgia—not simply a longing for a lost past, but rather an act of remembering that is imperfect, a dialectical process that looks backwards even as it participates in constructions of the self that are oriented towards the future—underwrites Schoenberg’s engagement with the past and anxiety about the future. His waltz arrangements, celebrating the pinnacle of Viennese imperial culture, are contemporary with his foray in dodecaphony, and as such curiously anachronistic. But, as I argue here, considering Schoenberg as a nostalgic—via the work of cultural theorists like Svetlana Boym—opens the door to some possible different narratives for music history. Schoenberg’s legacy of “crisis and progress” can thus be challenged, and something like Boym’s “third way” of modernism, with its “lateral possibilities,” can emerge.