Nearly a decade ago, the author of this book cofounded the University of Virginia's SpecLab, a digital humanities laboratory dedicated to risky projects with serious aims. This book explores the implications of these radical efforts to use critical practices and aesthetic principles against the authority of technology based on analytic models of knowledge. Inspired by the imaginative frontiers of graphic arts and experimental literature, and the technical possibilities of computation and information management, the projects the author engages range from Subjective Meteorology to Artists' Books Online to the as yet unrealized Paracritical Demon, an interactive tool for exposing the structures that underlie our interpretations of text. Illuminating the kind of future such experiments could enable, the book functions as more than a set of case studies at the intersection of computers and humanistic inquiry. It also exemplifies the contention that humanists must play a role in designing models of knowledge for the digital age—models that will determine how our culture will function in years to come.