This dissertation, based on ethnographic and archival research, examines the entanglements of race, space, and musical practice on Chicago’s South Side jazz scene. Drawing from research in ethnomusicology, jazz studies, urban geography, critical race theory, and oral history, it argues that the spatial conditions of urban centers inextricably intertwine with social relations and culture and are therefore crucial factors shaping musical practices and scenes—cultural formations that sustain such activities as live performance, artistic growth, and audience participation. Across jazz scenes, venues—in African American neighborhoods, downtown business centers, or majority-white areas of a city—are valued places where musicians, audiences, and others co-create the music’s changing practices and the scene’s social life. Through three case studies that highlight the interplay of space, memory, culturally grounded pedagogy and musical practice in Chicago, the dissertation shows how, through long-term social interactions, musicians and audiences negotiate changing historical and artistic currents while strengthening their ties, deepening their knowledge and remaking their social worlds. Chapter 1 analyzes the exploitative conditions that black musicians endured from the 1920s to the 1960s while working within and across racial boundaries. Chapter 2 presents a history of the contributions of the black musicians’ Local 208 in empowering, and sometimes exploiting, black musicians as laborers. Chapter 3 studies how venues organize scene knowledge by using an interview method called “the stroll” where musicians are driven to the sites of bygone venues and their stories recorded. The next two chapters present a case study of the New Apartment Lounge, a South Side venue that was home to a celebrated weekly jam session hosted by saxophonist Von Freeman whose quartet included this author on guitar from 1997 to 2012. Chapter 4 examines the experiences of musicians who often participated in the jam session and how they use what they learned from Freeman in their present practice. Chapter 5 discusses the ways in which the club’s audiences co-authored performances through material, emotional, and musical support of Freeman. Four premises underlie the case studies—that race and space are mutually constitutive social processes; that these processes both constrain and enable musical labor; that place functions as an epistemology that shapes musical, social, and cultural knowledges; and that music scenes have the potential to disrupt local spatial configurations.