This dissertation is about a collection of musical repertories—broadly speaking, American experimentalism—and the practice of music analysis. In many ways, the two do not go hand in hand: music analysis has long found itself confounded by experimental traditions, in some cases writing them off altogether. I argue that this tension is no coincidence but a matter of design. Composers of experimental music were paradigmatically concerned with the breaking and recasting of cultural norms and practices—of performance, listening, composition, and the medium of music. It thus comes as no surprise that the discipline of music analysis found itself breaking against these repertories. I contend, however, that these sites of breaking should not be abandoned but encountered as a productive field of conflict with the potential to recast both experimentalism and music analysis. The analytical approach I develop draws from disciplinary perspectives of music theory, art history, and literary criticism, and takes up three main themes: technology, culture, and analysis. Technological innovations in the twentieth century changed the way composers thought about and created musical sound; within the dissertation, I argue that experimental composers also used their musical works as technologies for the redefinition of important musical concepts, and for the breaking and recasting of cultural norms and practices. Listening closely to their works and cultural interventions leads to a reflexive analytical perspective in which music theory can rethink its disciplinary methods. In Chapter 1, theories of form and conceptual art intersect in a music-analytical vignette of John Cage’s 0′00″ (1962). In Chapter 2, I argue that, through his indeterminate musical works, Cage composed a listening subjectivity for his audiences. Chapter 3 centers on the use of mechanical repetition to develop alternative listening practices in Pierre Schaeffer’s musique concrète and Steve Reich’s early minimal music. In Chapter 4, I suggest that Reich’s It’s Gonna Rain (1965) replaces the anthropomorphism of classical music with technomorphism through abnegations of agency and voice. Finally, I consider how the music of Julius Eastman and Maryanne Amacher can productively challenge experimental music’s predominant ways of listening and music theory’s ways of conducting analysis.