This article based on primary research including collections from the Alan Lomax Collection from the Library of Congress’s American Folklife Center, The Chicago Historical Society, The Pullman Company Papers from the Newberry Library, and the recently discovered Michael van Isveldt Collection from Amsterdam, Netherlands, argues that within Chicago’s rapidly developing Black Metropolis between World War I and II, Chicago bluesman Big Bill Broonzy treaded lightly between a world of black and white "Old Settler" ideas and those brought from the South by migrant "New Settlers." By doing so, he helped establish a new dimension of the Great Migrations to Chicago’s Black Metropolis that centered on black creativity and a new kind of entrepreneurialism. This new dimension, moreover, nurtured a new identity in the emerging black urban consciousness that involved, in equal parts, southern cultural pathways and new ones created by city life. Scholarship on the development of Chicago’s Black Metropolis and the Great Migrations to the Windy City has viewed the development of race and class dynamics in terms of power negotiations between Old Settlers, African Americans who arrived to Chicago before World War I, and New Settlers, who arrived after. Each group’s respective approaches to community development, class formation, and racial respectability often clashed. To many scholars of the Black Metropolis, most African Americans fell into one of these two camps and many of the studies on these intercommunity dynamics place the problem in a negative light. An examination of Broonzy’s life in Chicago, however, demonstrates that the lines of power and personal politics in the city of Chicago were fluid and he learned to navigate the city by pushing the boundaries of race, class, and public respectability. By pushing these boundaries, moreover, Broonzy developed an identity based on his blues persona that exemplifies African American community and identity development within an urban environment that moved beyond migrants’ industrial labor purists. Broonzy and probably many others straddled both sides of the Old Settler–New Settler paradigm. A laborer by day and musician by night, Broonzy navigated these two spheres with ease, and he, therefore, reveals an entirely new component of community development within the Black Metropolis.