The potentials and problems of the digital and analogue environments need to be oriented into critical theories of information, knowledge, entertainment, pleasure and education. David Lowenthal (1985), just fifteen years ago, argued that the past is a foreign country. Increasingly though, it is the present that is becoming a tourist destination. The most significant analytical task for contemporary critics is to disrupt the dual ideologies punctuating the now: inevitable technological change and progress (1). Only then, may theorists ponder the future of a digitised past. This paper investigates how digitisation challenges not only knowledge workers such as archivists and librarians, but raises the dilemma of obsolescence and the role of nostalgia in policy decisions. Disempowered groups, denied a voice and role in the analogue history of the twentieth century, will have inequalities reified through the digital archiving of contemporary life. Notions of preservation, cataloguing and the structure of knowledge will be considered in the new/old intellectual environment. The final part of the paper investigates the formation of a virtual middle class, arguing that digitisation is actually and actively reinforcing the social exclusions of the analogue world.