In this article, the authors examine the history and current state of the diverse landscape of Russian rap music. An overview of the evolution of hip-hop summarizes how the genre emerged in the mid-1980s as part of the broader underground movement. In the 1990s, the drastic change in the sociocultural context was followed by the dissolution of the Soviet counterculture represented by music genres such as rock and rap. Based on this historical context, the authors examine the esthetics and cultural significance of contemporary Russian rap as a possible cradle of a new musical countercultural movement. Using the example of Russian rappers from the periphery such as Dmitrii ‘Husky’ Kuznetsov, the authors discuss the nature of the emerging musical underground and draw parallels with the musical landscape of the late-Soviet Siberian underground. Finally, the article lays the foundation for further research on the development of Russian underground culture under the conditions of the restoration of the country’s authoritarian politics.