With the aim of unravelling the role of popular culture in contemporary Caribbean writing, this essay focuses on how calypso, carnival and dancehall cultures have been used in the work of post-millennial Caribbean writers to examine issues of gender and sexuality. Caribbean writers employ innovative textual strategies, which draw thematically and stylistically from music and carnival. These textual strategies challenge the perceived boundaries between oral and scribal and between ‘high’ and ‘low’ cultures, and they can create a platform from which to challenge misogyny, patriarchy and social injustice in the contemporary Caribbean and beyond.