This essay focuses on the Pierrot and the Pisse-en-lit Carnival characters during the 1880s and 1890s. Pierrots rambled on about recondite events; spelled out convoluted words in a show of their supposed wisdom; and brawled with other Pierrots to commandeer streets. As to the Pisse-en-lit, these often-transvested revelers displayed bloodied clothes; exposed their underwear to passers-by; simulated sexual intercourse; carried chamber pots on their heads; and/or held sticks protruding from between their legs. The article outlines Trinidad’s historical context and features sections on both the Pierrot and the Pisse-en-lit, followed by a brief conclusion. The Pierrot and the Pisse-en-lit were part of an unsettled cultural arena which was adjusting to unbridled migration to the cities, the consolidation of a Black middle class, and the growth of Victorian morality. Both born from and broken by the conditions of the nineteenth century, the figures emerged out of fraught circumstances, meeting their demise as those circumstances decisively shifted.