In this dissertation, I focus on the ways in which improvisers produce interactive systems through their daily work. I argue that musicians within jazz rhythm sections engage in consistent processes of negotiation and compromise in their development of musical systems, and that stylistic change in jazz reflects changes in the interactive patterns of improvisers. I trace the development of localized interactive systems, beginning with a consideration of cognitive processing and social organization within local performance networks. As the dissertation progresses, I work concentrically outward to address the ways in which the work of specific rhythm sections is shaped by their engagement with bandleaders, the recording industry, the critical establishment, and audiences. In this study, I explore four spatially and temporally specific case studies, engaging with the work of musicians active from the 1930s through the early 21st century. I begin with a discussion of a small network of musicians currently active in New York's East Village, revealing the ways that their community has been shaped by their shared histories and their commitment to improvisational process. In addressing the constraints imposed on interactive processes by bandleaders and recording industry personnel, I focus on the Blue Note label in 1964. I consider the roles of jazz critics and radio networks through an exploration of the development of a national jazz mainstream in the late 1930s. Finally, I outline two distinct approaches to the development of Latin Jazz in the late 1940s, and I address the influence of particular venues and audiences on the interactive approaches undertaken by each ensemble. Through ethnographic inquiry, archival research, and close analysis of recordings, I address the local development of interactive systems and emphasize the compromise and contestation so central to the music's production. Drawing on recent research in anthropology and the social sciences, I explore the collective work and play of knowledgeable cultural actors in developing, maintaining, affirming, and challenging distinct systems of musical interaction. Through this work, I assert that the music's stylistic history should be understood as a history of practice, fundamentally tied to the daily work of musicians.