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This dissertation comparatively examines musical nostalgia, particularly nostalgia for childhood, in video games and post-Romantic classical music. An introductory chapter lays out several key concepts drawn from video games—loops, gameworlds, and role-play—and suggests the correspondences these have in Romantic music and thought. The central chapters offer case studies of pieces by Robert Schumann, Brahms, Debussy, and Ravel, each along with a corresponding concept drawn from video games. Each chapter articulates ways that works by these composers provide analogies for practices in contemporary role-playing and adventure video games and, conversely, suggests that features drawn from those games might illuminate how these pieces create musical meaning out of dwelling on the past or imagining distant places. The central chapters draw video games and classical music more closely together over their course. In an analysis of Schumann’s Kinderszenen, I suggest that Schumann’s music could be conceived as offering the player a form of role-play, allowing its players and listeners to play as an imagined child and gain access to otherwise inaccessible space. Brahms’s works often dwell in the past (and are often analyzed as such), especially when that past is metaphorically conceived as childhood or the classical tradition. I suggest that we might hear Brahms’s music as preoccupied with the “unrevisitable location,” a feature of video games in which certain spaces are visitable only a fixed number of times and therefore charged with melancholy and loss. Debussy’s Children’s Corner extends role-play to an extreme degree, while at the same time suggesting distant, unreachable vistas. In particular, I borrow Jay David Bolter and Richard Grusin’s ideas on mediation and Christopher Goetz’s notion of “nostalgic travel” to suggest ways that Debussy’s music incorporates impossible distance into its sound and structure. Video games and classical music converge as much as possible in an analysis of Ravel’s Ma mère l’Oye, which I read alongside Nintendo’s open-world game The Legend of Zelda: Breath of the Wild. I suggest that Ravel’s music offers space for its players to explore similar to this video game. In particular, we might hear the music as allowing linear narrative to give way to a freer, open-ended exploration, suggesting the opening of a world. Finally, a concluding chapter examines nostalgia in video games themselves, specifically Undertale, Final Fantasy VII, and Final Fantasy VII Remake, while revisiting elements of the Romantic musical past as they have accrued in the dissertation so far. The argument in this final chapter is that of the dissertation as a whole: that the same desires for fantasy and adventure animate both traditions, and that the two provide meaningful contexts for each other, in ways that studies of the two have until now overlooked.