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Historians have described Pittsburgh’s historically Black enclave, the Hill District as “Pound for pound...the most generative black community in the United States.” From its offices in what Claude McKay once called the “crossroads of the world” The Pittsburgh Courier, for instance, transformed African Americans relationship to the white press, with its national circulation concerning Black struggles for citizenship around the globe. Courier Photojournalist Charles “Teenie” Harris captured depictions of life in the Hill District, “now considered the premiere depiction of African American urban life during the peak of the industrial era and the early onset of deindustrialization.” Residents of the Hill created a thriving cultural sphere most famously preserved in August Wilson’s Pittsburgh Cycle. The series of ten plays chronicles 20th century African American life, most of them taking place in Pittsburgh’s Hill District—including the two which won Wilson a Pulitzer Prize. The jazz clubs on the Hill produced acclaimed musicians Earl “Fatha” Hines, Mary Lou Williams, Billy Eckstine and Billy Strayhorn, as well as their young prodigy, Lena Horne. From the literary arts of August Wilson and John Edgar Weidman to the visual arts of Henry Ossawa Tanner and Romare Bearden, this paper places the cultural production of 20th century Pittsburgh within a broader tradition of the Black Arts as an archive of Black life in America’s urban centers.