Throughout the colonial period in America, and into the nineteenth century, cooks without ovens often prepared cakes in cast-iron skillets on their stovetops. Even as late as 1943, The Joy of Cooking included a recipe for an upside-down cake made entirely in a skillet.
Upside-down cake’s antecedents were likely the cake-like puddings or cobblers that became popular toward the end of the nineteenth century. They had fruit on the bottom and a very plain yellow cake—often called “cottage pudding”—on the top; some were inverted for serving. Early-twentieth-century cookbooks featured recipes for upside-down cakes using apples, cherries, and other stone fruits, but the cake surged in popularity in the 1920s, when canned pineapple became chic, thanks in no small part to aggressive marketing by the Hawaiian Pineapple Company. Pineapple rings were placed in the butter and sugar mixture to caramelize over heat, with a maraschino cherry—another newly fashionable ingredient—set in the center of each ring. After baking, the cake was carefully inverted onto a serving platter to reveal the decorative pattern on top.