In this study, I analyze the significance of Shakespearean intertextuality in the major works of Thomas Wolfe featuring protagonist Eugene Gant: Look Homeward, Angel and Of Time and the River. Specifically, I explore Gant's habits and preferences as a reader by examining the narrative arising from the protagonist's perspectives of Shakespeare's The Merchant of Venice, Hamlet, and King Lear. I examine the significance of parallel reading habits of Wolfe the author and Gant the character. I also scrutinize the plurality of Gant's methods of cognition as a reader who interprets texts, communicates his connections with texts, and wars with texts. Further, I assess the cumulative effect of Wolfe's having blurred the boundaries between fiction and reality, between the novel and drama. I assert, then, that Wolfe, by incorporating a Shakespearean intertext, reveals aspects indicative of postmodernism.