This thesis explores drag as a fascinating performance medium with a rich and complex history. The thesis is presented as intertextual, comprising two parts: a body of creative works and a written paper. Drag as a male cross-dressing performance is documented to contextualise contemporary drag as an important LGBTIQA+ performance medium. During gay liberation, drag had been a form of entertainment with a defiant socio-political ethos used for resistance, fun & survival. The question set out in the paper is: how can a theory of drag explore drag as a site of carnival to elucidate new ways of looking at sex, gender & sexual orientation? Drag is proposed as a carnivalesque performance framed as a conceptual lens viewing drag as grotesque carnival, initially theorised by Russian writer Mikhail Bakhtin, who explained carnival as having roots in pagan ritual where there is a dissolution of order, the destabilising of boundaries, and an abandonment of rules. As drag is a cross-dressing transformation simultaneously embodying the representation of both sexes, the drag persona is a form of carnivalesque mask, and this is explored as a metaphysical experience linked to ancient theatre, occult ritual, & grotesquery. For gay culture, artistic risk-taking and a radical rethinking of drag created the emergence of a grotesque aesthetic caused by a state of community grief, anxiety, and fear amid mass death from HIV/AIDS. This era also created conditions for the emergence of a queer identity, as a call to arms in the fight against HIV/AIDS and homophobia. Queer and queer theory is used in this thesis to explore a novel way of reimagining drag. A chapter is dedicated to Ballroom culture, a drag-centred movement started by LGBTIQA+ Black & Latino communities in the US. The exploration of the Carnival Drag Grotesque in this thesis will offer a deeper insight into a fascinating medium, steeped in ancient ritual & tainted with its own polemics, bringing drag to a material/mystical nexus.