Upside-down cakes date to the late 1800s, when cooks used skillets to make cakes because ovens were not yet reliable. But the pineapple upside-down cake first appeared in the 1920s, when Jim Dole, founder of the Hawaiian Pineapple Company, started canning up to 95 percent of his crop. This practice brought the once exotic fruit into the mainstream. When the company held a cooking with pineapple contest in 1926, more than 2,500 of the submissions were for pineapple upside-down cake.
New culinary tools also made their way into cookbooks. Roberta Ames, author of The Complete Electric Skillet-Frypan Cookbook gave a nod to Reynolds Wrap in her pineapple upside-down cake recipe when she wrote, “The Reynolds Home Economic Staff suggested the use of foil in upside-down cake. This method does beautifully, and the cake is easier to remove than if baked right in the pan.” It does indeed work beautifully, and this adaptation of Ames' pineapple upside-down cake includes this helpful tip.
Preheat the oven to 350 degrees.
Line a 10-inch cast-iron skillet with aluminum foil, completely covering the bottom and sides and extending extra foil over the edges of the pan. Place the butter in the skillet and transfer to the oven. As soon as the butter is melted, remove from the oven and stir in the brown sugar, carefully mixing well with a rubber spatula so as not to tear the foil.
Arrange the pineapple slices over the butter-sugar spread. Place cherries in the center of the pineapple and pecans between the slices.
In the bowl of an electric mixer, cream the butter, adding the sugar gradually, and then add the eggs and beat well. Stir the flour, baking powder, and salt together in a small bowl. Combine the buttermilk, syrup, and vanilla extract in a small measuring cup. Add the flour mixture alternately with the buttermilk-syrup mixture, beating well after each addition. Spread the batter evenly across the mixture in the skillet.
Place in the oven and bake for approximately 45-50 minutes, or until a toothpick inserted into the center of the cake comes out clean. Place a large cake plate over the pan, and invert to remove. Peel off the aluminum foil, pressing back any pineapple that may be stuck to the foil.