This chapter situates the black intellectual Horace Cayton into the vibrant community of Chicago's South Side during the Depression and World War II era. It details the research projects undertaken by Cayton in Chicago, including his labor scholarship and journalism, Cayton-Warner and WPA projects, and ultimately his crowning achievement: the coauthored 1945 Black Metropolis. In charting this flurry of activity, the chapter shows how Cayton never felt satisfied with his position in the black elite and the Chicago School of Sociology. To broaden his activities among working people and artists, Cayton managed the Parkway Community House that he fashioned into a central hub for the black arts movement. The programs, protest meetings, and cultural events at the Parkway House reflected the personality of Cayton, who crossed boundaries of class, race, and respectability.