This paper analyses deceiving and self-deceiving aspects of society in Stanley Kubrick’s films, which illustrate the problems of enlightenment from the perspective of critical theory and poststructuralism. A Space Odyssey registers the source of Nietzschean power relations in human nature. A violent humanity is the foundation of the one-dimensional Cold War society and welfare state, where misinforming the communists or its own population is justified by a “higher cause”. Political interests deliver their own version of the truth. Pseudo-individuality and conformity are present not just on this very planet, but also among astronauts in space. The film also shows a countercultural opposition, and the critique of it is further developed in A Clockwork Orange. Kubrick does not accept a classic Marcusean view of the second dimension. The Nietzschean nature forms both language and action of youth subcultures, and the difference between the good and the evil is rhetorically blurred. Aggressive hero becomes the victim of Foucauldian prison discipline, and for Kubrick its consequence is the loss of free will to make moral decisions. By prohibiting lying and violence, i.e. by “normalizing”, good behaviour stops being an action of free will. Also, cruelty of the main character becomes a public virtue (Horkheimer and Adorno’s totalitarianism), and becomes useful to the social elites. Calculative and sadistic aspects of enlightenment are brought in collision, with no clear resolutions, forming life in the risky and reflexive modernity. Kubrick’s dialectics of enlightenment caries a cynical implication that lies and violence are both enemies and constituents of enlightenment.