The main question this article attempts to answer concerns the nature of conditions that would signal the possibility of reemergence of totalitarianism in the Western civilization. The article focuses on socio-psychological consequences of new systems and technologies of surveillance that regulate access to various - state, public, market, private etc. - spaces of choice and opportunity. A notable by-product of these systems can be described in terms of information clusters that assume a role of our virtual clones, or external surrogates, of ourselves. In everyday life, their condition may have even more significant practical consequences for us than the state of our proper self. The article analyses the potential analogies between the virtual clones and the secret files of totalitarian regimes. It also proposes a new concept of surveillance-directed character type, thereby extending David Riesman's classical typology of social types. Other issues explored in this article include: the potential of new technologies to merge and centralize diverse data systems; social atomization and a tendency to replace social spaces with new forms of fictitious, virtual reality; post-totalitarian tendency to negate epistemological distinction between truth and falsehood; and the preference of multi-cultural societies for replacing moral normativity with procedural liberalism. One of important, though paradoxical, effects of these processes in Western democracies is strengthening of authority of the knowledge generated by secret services and other risk-defining agencies. This leads to extreme cognitive-legal positivism which is an important element of rapidly expanding surveillance culture..