This dissertation uses new media theories and developments in entertainment and publishing media during the first decade of the century in progress to argue for the significance of the fiction and multimedia projects of a new generation of American novelists. This set of novelists - Michael Chabon, Dave Eggers, Jonathan Lethem, and David Foster Wallace - have adapted to radical changes in literary production and consumption in order to imagine new approaches to literary aesthetics, entertainment, and questions of audience in the new millennium. These novelists conceive of themselves as a new generation that has developed out of and in reaction to the legacies of the postmodern fiction that preceded their generation. As importantly this generation is aware of its consideration of new aesthetic strategies that recognize enormous modifications in the cultural relationships between fiction and media over the last decade. A comparison with a representative postmodern novelist (Thomas Pynchon) demonstrates the extent to which this new generation of novelists offers exciting and unique new directions for literary fiction and for the study of contemporary literature in this era.