This paper examines the transformation of digital futures through two Brazilian songs: Gilberto Gil's Pela Internet (1996) and Caetano Veloso's Anjos Tronchos (2021). Read together, they illuminate a broader shift from early imaginaries of openness, participation, to a platformized environment structured by data extraction, infrastructural concentration, and asymmetrical dependencies. This shift relocates political struggle from communication to governing the infrastructures of data, AI, and platform power. Drawing on theories of countergovernance, it examines how collective action can challenge concentrated platform power through reciprocity and commons-based infrastructures. Adopting a conceptual and interpretive approach, it treats the songs as historically situated interventions while positioning Brazil's free culture movement as a concrete experiment in commons-building. In doing so, it positions Brazil as a place one thinks from, not only about: a site revealing both the possibilities and fragility of institutionalized commons while offering political repertoires for contesting platform power and reimagining digital futures.