Anchored in rich archival material, this chapter explores the diverse performance centers; dramatic genres; and key writers, actors, metamorphosing stock characters, and forms of humor that marked theater in Cuba’s long nineteenth century. Drawing on the growing diversity of Havana audiences for theatrical entertainment, interwoven with the stereotypes of ethnicity, race, and social class that often peppered theatrical genres, the chapter frames its detailed examples within the larger questions posed by a literary history, including whose theater history should be told and, in the context of the widely located political, economic, and commercial forces marking the island’s history, to which geographies and colonial or national temporalities its nineteenth-century theater history should belong.