The aim of this article is to approach from a cultural history perspective the dissemination and propaganda work carried out through music by the Communist Youth of Chile (JJ.CC.) and the Manuel Rodríguez Patriotic Front (FPMR), within the framework of the Popular Mass Rebellion Policy (PRPM) promoted by the Communist Party (PC). Under the clandestinity that the Chilean civil-military dictatorship meant for the leftist political parties, different strategies of resistance to the regime and dissemination of the political project were developed, among them the production of music on cassette. Here we highlight “El Camotazo” (JJ.CC.) and “En medio del combate… cantamos” (FPMR). Both works captured the main generational guidelines of the Popular Rebellion, strengthening an imaginary around self-defense and confrontational struggle, especially armed. These works show a combination of the old practices of communist culture and the new elements brought about by the 1980s: diffusion and insertion of the masses through cultural strategies (in this case, music) and the new allegories of revolutionary political violence exercised in the context of the Popular Mass Rebellion. Based on the above, we seek to analyze the experience of both works and the role they played in the strengthening of the Popular Rebellion, gestating and sharpening those new perspectives of struggle in Chile.