This essay examines the meanings of gender in the music of Cuba’s Nueva Trova, an important expression of what came to be known as the Nueva Canción (New Song) that flourished throughout Latin America between the 1960s and the 1980s. The continent-wide movement sought to challenge the commercialization of the airwaves by raising profound, revolutionary, and deeply Latin American themes while revaluing traditional instruments and styles. Music played an important role in articulating a rejection of capitalist and colonial values, a turn to popular and indigenous roots, a commitment to continent-wide revolution, and a vision of a better world. Through festivals, gatherings, and conferences, mass concerts and radio, international travel, and, under dictatorship, clandestinely circulated cassette tapes, the Nueva Canción exemplified a generation’s search for multiple meanings of liberation. In participating in radical critiques of Latin America’s social order, the Nueva Canción rewrote gender norms embedded in society and its music. Revolutionary singer-songwriters explored the meanings of human emancipation in ways that challenged traditional gender roles and ideologies. Political, personal, and love songs upended gender stereotypes to offer new, revolutionary meanings to romantic love. Songwriters linked the Cuban Revolution to other Latin American revolutionary processes and imagined how the new society would liberate the human spirit and human potential. Socially committed art reflected, explored, and contributed to imagining the new world, and reimagining gender played a role in the process and in its music.