August Wilson’s plays show his ability to draw upon and transcend the turbulent years he spent at his now-famous Hill District address at 1827 Bedford Avenue. With the benefit of time and distance, Wilson wrote a series of compelling dramas that speak not just to the tensions within a single Black family but also to conditions faced by the Black masses still impacted by the trauma of slavery and the effects of cultural fragmentation. We thus see in Wilson’s series of symbolic and sometimes clearly allegorical characters evidence of an overarching narrative about the counterbalances between forces that set Black families asunder and the resilience that reunites and bonds them together. This chapter explores the ways Wilson’s plays demand that we regard “family” in both literal and figurative terms through an analysis of the Black family portraits on display in them.