In 1985, Italo Calvino proposed six values he deemed crucial to literature as it moved into the next millennium: lightness, quickness, ‘crystal’ exactitude, visibility, multiplicity, and consistency. Using Italo Calvino’s Six Memos for the Next Millennium as structure and methodology, this book conjoins literary studies with creative practice to interrogate, extend/subvert, and then reflect on the aesthetic and structural ambitions of multiple innovative print authors (Italo Calvino, Zadie Smith, William Faulkner, Virginia Woolf, Bernardine Evaristo, Roberto Bolano, Rachel Cusk, Shahriar Mandanipour, W.G. Sebald, Ross Gibson, Han Kang, and J.M. Coetzee) reimagined in new media in order to develop a model for digital literary practice-led research. This work contains four strands that are presented simultaneously. First, this monograph explores the rise of Calvino’s values within the Calvino corpus. Second, this value’s application to a contemporary literary predicament is explored through a digression. Third, conclusions from this interrogation are drawn as they relate to digital literary culture. Finally, the value’s importance is demonstrated through examining/reflecting on contemporary digital literary creative practice – both the author’s own and works created by contemporary writers/artists who have engaged with the digital postmodern.