This paper compares Dostoevsky’s The Gambler (1866) to certain features of Thomas De Quincey’s Confessions of an English Opium Eater (1821) to show that the two texts demonstrate the emergence of a simulacral culture of the modern self. The De Quincean model of subjectivity is presented as a prototype of the modern self before The Gambler is investigated in its light. Insofar as the self is constructed in the context of social environments, modernity is characterized by a mimetic mode we might call intensity, where the modern self finds and creates its identity through repetitive patterns of mediated experience. In particular, it is argued that the first-person narrators of Confessions and The Gambler exemplify the obsessive cycle of self-production—a characteristically modern addiction to the decentring and multiplication of the self, rooted in the need for the intoxicating effect of strong sensations and imaginary experience. Self-production functions in a cycle of passion, transgression, and suffering, followed by anticipation of change and renewal, on a par, psychologically, with rebirth or resurrection. The major difference between the works is that, while Confessions emphasizes the causality of social conditions, The Gambler is predicated on the uniquely Russian sense of destiny (sud’ba).