This article, through a musical, lyrical, and contextual analysis of the Irish recording artist Damien Dempsey’s song “Colony,” probes contemporary discourses concerning colonialism and postcolonialism. In presenting Dempsey’s work through this lens, we seek to interrogate how one singer employs protest song as a vehicle for social critique in a nuanced fashion. Our reading reveals different levels of meaning, in part dependent on contextual knowledge. Furthermore, the simple structure belies the complexity of the issues involved in any discussion of postcoloniality in Ireland and beyond, and because of this the song is rendered all the more potent and persuasive.