Sounds that Fall Through the Cracks, and Other Silences and Acts of Love tells the story of a dozen cosmopolitan socially aware singer-songwriters, poets and musicians of different racial, ethnic and national backgrounds who developed their political consciousness by thinking within/through the colonial problematic of Québec or Puerto Rico in the 1960s and 1970s. Five interrelated claims give coherence to this work: a) grasping the decolonial import of socially aware repertoires needs to attend to the meeting point among sound, music, lyrical content, and the interlocutor’s perspective on the musical object; b) understanding the historical contexts which shaped each interlocutor’s life is necessary to fully comprehend her political-aesthetic choices; c) when incorporating the interlocutor’s way of imagining the past one must pay attention to the ways in which that past has been historicized d) reflecting on how the other is inscribed in sound and word needs to account for how that other envisions herself and; e) these critical assessments must be developed “theorizing with your interlocutor” in a relentless back and forth informed by love and friendship that takes seriously the critical import of the interlocutor and considers his needs and desires. Combined, these claims are conducive to a critical analysis that is historically rigorous, ethical and fair to the interlocutor and the other to the extent that the unavoidable limitations of the researcher allows for. By departing from spaces where the eye meets the ear, logos and phono entwine, the historical context shapes the musical object and vice versa, fieldwork and life are fused, and the interlocutor is treated not only as a producer of culture but as a thinker in her own right, I problematize four major categories: Puerto Rican nueva canción (PRNC), chanson québécoise (CQ), the related anticolonial narratives that frame these musics, and the category “the decolonial.” Regarding the latter, I pay careful attention to the relationship between bodies of knowledge around the colonial, such as postcolonial, Latin American decolonial, settler colonial and anticolonial studies. Edouard Glissant has argued that “generalization” is one of the manifestations of a “totalitarian root” because “from the world it chooses one side of the reports, one set of ideas, which it sets apart from others and tries to impose by exporting as a model” (2010 [1990]: 20). Inspired in part by the Martiniquais philosopher and poet, my overall argument is that decolonizing knowledge must involve a collective praxis of “theorizing with your interlocutor” that in addition to assessing how colonial logics are reproduced and proposing ways to contest them, must challenge the “totalitarian” and individualist “root” of academic discourse. In order to develop this collective praxis, I walk hand in hand with my interlocutors/friends Américo Boschetti, Frank Ferrer, Bernardo Palombo, Jesús Papoleto Meléndez, Hilcia Montañez, Oscar Pardo, Sandra María Esteves, Suni Paz, Sylvain Leroux, Marie-Claire Séguin, Rouè Doudou Boicel, Lise Vachon and Georges Rodriguez, and other decolonial and anticolonial thinkers.