This chapter details and reflects on some of the pedagogical strategies I deploy to demonstrate for students in my general education/core courses why and how theatre still matters. More specifically, it explores how I draw on and engage work by African American playwrights—Lorraine Hansberry and Robert O’Hara, in particular—to examine the ways theatrical texts and performances can serve to engender and enable “reality checks” that invite audiences to interrogate their assumptions and, indeed, imagine fresh possibilities for effecting change. Much of the work that emerges out of the African American theatrical tradition is ripe for getting students to attend to and reckon with some of our most pressing and vexing societal issues and concerns. This chapter sharpens particular focus on how I analyze two plays from this tradition, Hansberry’s canonical family drama A Raisin in the Sun and O’Hara’s cheeky domestic comedy Barbecue, with my students to demonstrate the significant role that theatre and performance continue to play in shaping how we come to understand and respond to important social, cultural, and political events and phenomena.