The popular genre of sung and spoken performance—naniwabushi—was the biggest ‘craze’ during the first decade of the twentieth century in Japan. This article uncovers how Miyazaki Tōten (1870–1922), a revolutionary and thinker who became a naniwabushi balladeer, was instrumental in the rise of naniwabushi as a popular art form during the Russo-Japanese transwar period (1902–1909) and used it to engage in a practice of nihilist democracy. In using a transwar frame to examine the content, audiences, and contemporary reports of his performances, this article concludes that Miyazaki Tōten created ‘new’ naniwabushi to deliberately link the techniques and rhetoric of the Freedom and People’s Rights Movement from the 1880s to the Russo-Japanese War (1904–1905). He used naniwabushi to articulate his concepts of autonomous freedom, nihilism, and anarchist communitarianism in a time usually characterized by the heavy suppression of dissent. It counters the impression of the wholesale embrace of nationalism and support for Japanese imperialism and shows how Japan’s urban poor engaged in political discourse through popular entertainment that was critical of Japanese imperialism.