ABSTRACT August Wilson’s celebrated ten-play cycle in which he focuses on the African American condition during the twentieth century has been hailed for the way the playwright grapples with issues of history and identity. This paper adopts aspects of the New Mobilities Paradigm (NMP) as it carries forward the theme of alienation, confusion and despair in Wilson’s plays. It argues that Jitney and Two Trains Running deploy highly deceptive cause-to-effect linear plot structures in order to present African American characters who are caught-up or trapped in desultory predicaments of confinement in ways that echo tropes of memory, journeying, hope and despair. The two plays present interesting nuances and contradictions of tropes of journeying and entrapment as well as progression and stagnation, which are paradoxically connected to acts of self-assertion. This occurs in ways that are highly reminiscent of the modernist style of absurdism. Our choice of the two plays is informed by the way in which the play titles reference technologized forms of mobility and communication as they also echo African American memory, travel and the journey motif in ways that are reminiscent of the underground railroad and the promise of freedom, even as Wilson decries a palpable lack of movement, growth and social progress that has historically characterized the African American experience during the course of the twentieth century.