Much ink has been spilt worrying over the death of the book. It may be, however, that we find ourselves facing a situation where, as Whitman himself prophesies, “To die is different from what any one supposed, and luckier.” My dissertation tests the truth of this prediction by exploring the potential for digitization to create spaces where unexpected relationships between texts, authors, and readers may appear. The dissertation begins with an overview of several options for conducting literary history in a digital environment. I look at a number of sources for gathering information about Twain and discusses their potential. In the second chapter I proceed to an extended reading of data contained in a single digital source, the Chronicling America project. I discuss ways in which the data archived in Chronicling America may be used to suggest popular topics of conversation in the news at the time Mark Twain was working on his autobiography. The third chapter looks at how computer simulation can be used to stage interaction between Twain’s text and media accounts of the past. Together the chapters of the dissertation test the extent to which digitization invites new forms of literary inquiry, as well as the extent to which digital technologies may be united with printed texts to form the terrain for reading literature in the 21st century.