This article describes a successful experience teaching Wilder’s Pullman Car Hiawatha to theater graduate students at the University of Colorado Boulder. Students read the play alongside Bertolt Brecht’s The Exception and the Rule and Langston Hughes’s Don’t You Want to be Free? They prepared a comparative analysis of the three plays, and then the author turned their attention to the character of Harrison, a Black man who serves as the Pullman car porter. The author outlined the major role that Pullman car porters played in civil rights struggles in the United States and observed that Wilder puts Harrison in charge of the stage near the end of the play. In discussion, students found other representations of race and power in the play; notably, these included Wilder’s allusion to histories of Native American displacement. They also explored perspectives drawn from ecocriticism, disability studies, and critiques of modernity.