Set and costume designs are a large part of worldbuilding for the plays that actors inhabit. These elements enhance and contextualize the historical, geographic, and temporal environments for the performance. August Wilson was incredibly detailed in what he asked for in his plays, not just from the actors but also from the designers. Constanza Romero and David Gallo are but two of the designers who have brought the world of Wilson’s American Century Cycle to full realization. This chapter features a conversation between Romero, Gallo, and Willa J. Taylor about their design processes and practices when working on Wilson’s plays.