Musicians, scholars, and even reference materials are surprisingly united in the contention that music and politics occupy separate spheres in Canada. However, we suggest that denying the intersection of music and politics in Canada potentially blinds us to the complex ways in which artists, mediators, and audiences—that is, produsers—participate in projects that are undeniably ideological. Indeed, we suggest that appreciating the entwined relationship of music, politics, people, and contexts for circulation is particularly important at a moment when the participatory culture that prevails on social media platforms is increasingly normalised and the authority of established knowledge sources breaks down in the face of “controlless” circulations of content that radically challenge our capacities to communicate across partisan lines. Our analysis takes the form of three case studies: Tony Turner’s “Harperman” (2015), Adrian Sutherland’s “Politician Man” (2019), and Brock Tyler’s “Speaking Moistly” (2020). Our analysis interprets each example according to musical form, lyrics, creator intentions, and genre affiliations but, critically, also addresses how contexts for circulation, curation by produsers, and the affect of musicking illuminates kaleidoscopic meanings that accrue through the complex interactions of music and politics—meanings, notably, that cannot be discerned through a focus on the musical object or political landscape alone.