This article, which analyzes 136 of Silvio Rodríguez's over 500 songs and provides a close reading of seventeen, highlights musical patterns that recur in songs with similar themes across three periods: 1967-1970, when Rodríguez was censured; 1971-1989, when nueva trova became institutionalized; and post-1990, in Cuba's Special Period. Differing viewpoints and emotions are often set in different keys ("Debo partirme en dos" (1969)); songs with a political message are set in simple repeating patterns ("Resumen de noticias" (1969)); and many of his love songs are highly chromatic or harmonically unstable ("Ojalá" (1969)). Double-plagal progressions often signify fatalism and never-ending struggle ("Sueño con serpientes" (1974), "Reino de todavía" (1994)). Analyses are complemented by Rodríguez's comments regarding his creative process.