This dissertation examines the career and music of Harlem drummer and bandleader William Henry Chick Webb (1905-1939). Foregrounding Webb's connections with audiences, it emphasizes local circumstances and dialogic, co-creative performer-audience relationships. While many scholars mark 1935--when heavily arranged big band jazz became broadly popular--as the Swing Era's beginning, this project situates swing as a local genre in Harlem in the late 1920s and 1930s. Adopting conjunctural analysis from cultural studies, it emphasizes the particular sociopolitical and economic conditions in which Webb and other African American bandleaders and arrangers developed this music during the Great Depression. It explores the interplay between composition, improvisation, race, gender, dance, economics, urban geography, and political power through which Webb's deep sonic connections with local audiences developed. Adopting an interdisciplinary approach, the dissertation's three internal chapters are discrete methodological case studies that explore Webb and his music through spatial practice theory, carnal musicology, and critical discourse analysis. Spatial practice theory updates the classic jazz itinerary method--built here from over 1,000 clippings in African American newspapers--to follow how specific ballrooms and nightclubs, neighborhood dynamics, race and gender identities, political events, and ideologies informed Webb's tremendous stylistic diversity. Carnal musicology blends the author's experience as a vernacular jazz dancer with close readings of diverse historical source material and analytical tools from music theory to reconstruct and analyze Webb's live interactions with improvising lindy hop dancers at Harlem's Savoy Ballroom. Critical discourse analysis routes critiques of Webb and singer Ella Fitzgerald from white male aficionados in the emerging field of jazz criticism through queer theory and critical race theory to connect jazz's aesthetic system with broader structures of white supremacy, patriarchy, and class privilege. The concluding chapter blends these perspectives to analyze Webb's 1937 battle of music with Benny Goodman's orchestra. Ultimately, the dissertation advances an immanence-focused, rather than transcendence-focused, approach that can investigate figures whose significance, like Webb's, stems primarily from their popularity with specific audiences in particular times and places. Through this paradigm, jazz studies can disentangle itself from the uncritically transcendent narratives that entrench jazz history within problematic discourses of American exceptionalism.