Relating evidence from the mythological to the contemporary in both historical and media-archaeological registers, this article explores how techniques of sonic generation and representation shuttled between what might be defined as digital and analog domains long before the terms acquired their present meanings—and became locked in a binary opposition—over the latter half of the twentieth century. It proposes that such techniques be conceptualized via the “digital analogy,” a critical strategy that accounts for the nesting of techno-musical configurations. While the scope of digital analogies is expansive, the focus here falls on a particular interface and mode of engagement. The interface is the keyboard; the mode of engagement is the play, both ludic and musical, that the keyboard affords. Operations at the keyboard have been integral to ludic communication and computation as well as to the practices of composition, performance, and improvisation. To map out this genealogy and to show how it continues to inform loci of musical play from sound art to digital games, the article draws on an array of critical and theoretical texts including Friedrich Kittler’s media analyses, Vilém Flusser’s writings on technology, and post-Foucauldian discourses on cultural techniques.