During the masquerades common during carnival time, jumbies (ghosts or ancestral spirits) are set free to roam the streets of Caribbean nations, turning the world topsy-turvy. Modern carnivals, which evolved from earlier ritual celebrations featuring disguised performers, are important cultural and economic events throughout the Caribbean, and are a direct link to a multilayered history. This work explores the evolutionary connections in function, garb, and behavior between Afro-Creole masquerades and precursors from West Africa, the British Isles, and Western Europe. Robert Wyndham Nicholls utilizes a concept of play derived from Africa to describe a range of lighthearted and ritualistic activities. Along with Old World seeds, he studies the evolution of Afro-Creole prototypes that emerged in the Eastern Caribbean-bush masquerades, stilt dancers, animal disguises, she-males, female masquerades, and carnival clowns. Masquerades enact social, political, and spiritual roles within recurring festivals, initiations, wakes, skimmingtons, and weddings. The author explores performance in terms of abstraction in costume-disguise and the aesthetics of music, songs, drum-rhythms, dance, and licentiousness. He reveals masquerades as transformative agent, ancestral endorser, behavior manager, informal educator, and luck conferrer.