This article explores expressions of Russian masculinity in the Russian anekdot—a short humorous (and at times politically subversive) narrative that was highly popular during the late-Soviet era. Although anekdots challenged the legitimacy of Soviet power and highlighted inconsistences between propaganda and reality, they utilize and therefore reinforce categories and concepts of the very social system they contest. In conducting a paired content and discourse analysis of 1,290 Soviet-era Russian anekdots, this article demonstrates how this genre both (1) reveals a crisis in Soviet-era Russian masculinity and (2) contributes to a hierarchy of cultural citizenship established through the definition of particular racial, national, and gendered groups as "other." In doing so, the focus is not only on the objects of the jokes, individuals or groups that are scrutinized and ridiculed, but also on the subjects of the joke and the joke tellers themselves. This project demonstrates how Russian men are distinguished from Russian women as well as ethnic and national others through discourses of masculinity, femininity, and sexuality.