The author conducts a systematic comparative analysis of the scientific worldviews and key research ideas of the American political anthropologist James Scott and the Russian agrarian economist Alexander Chayanov, to show their similar interests in the study of peasant revolutions, state systems, and anarchist ideas. Based on the identified similarities and differences in the milestones of their intellectual biographies, the author compares Scott’s concept of the first ancient autarkic states with Chayanov’s abstract economic-mathematical models of island-states. The article describes the contradictions and failures of modern projects for transforming the nature and society by state bureaucracies as revealed in the studies of Scott and Chayanov, and emphasizes the interest of both scholars in the potential of the anarchist epistemological and political ideas for the development of the scientific theory and political practice of interaction between society and the state. The author argues that Scott and Chayanov are not orthodox anarchists insisting on the complete disappearance of the state; they believe that the Leviathan statehood is impossible and, perhaps, not necessary to destroy. However, in their research, both Scott and Chayanov constantly raise questions about the ways to limit and weaken the power of the state bureaucracy with various forms of non-state public life associated with the anarchist ideas of self-organization, spontaneity, and freedom.