This article examines the constitutive nature of Caribbean popular culture, specifically calypso performance, in postnational and postindependence identity formation. It seeks to contribute to research that highlights the importance of the work of the imagination in the active processes of community formations and intervene into standard calypso research and criticism that posits calypso as the voice of the people but identifies the people as a rigid, narrow, and bounded category. The article argues for full engagement with calypso within the context of carnival. It understands masquerade as a fundamental part of calypso performance and utilizes masquerade as an analytical category that permits us to understand the play of identities constituted within calypso performance. A masquerade analysis of The Mighty Gabby’s 2001 calypso competition finals performance exemplifies a case of a multivalent masquerade performance that specifically plays with discourses of sexual identity and provides clear insight into the aesthetic work of calypso.
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