Pineapple Upside-Down Cake is an American classic from the 1920s featuring a layer of caramelized pineapple rings and maraschino cherries baked beneath a moist, buttery sponge. Once flipped out of the pan, the fruit becomes a glossy, golden topping. The whole cake takes about 55 to 60 minutes to prepare and bake.
Preheat your oven to 350°F (175°C). While it heats, melt 1/2 cup of butter in a 10-inch cast iron skillet over medium heat.
Once melted, add the brown sugar and stir until dissolved. Arrange the pineapple slices over the sugar layer, then place a cherry in the center of each slice.
In a separate mixing bowl, sift together the flour, baking powder, and salt.
In another bowl, cream together the softened butter and sugar until light and fluffy, about 3 minutes. Beat in the eggs, one at a time, mixing well. Stir in the vanilla extract.
Gradually add the dry ingredients to the creamed mixture, alternating with milk, beginning and ending with flour.
Pour the batter over the arranged pineapple and cherries in the skillet.
Bake in the preheated oven for 40-45 minutes, or until a toothpick inserted into the center comes out clean and the cake is golden brown.
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Notes
Consider using fresh pineapple for a more natural taste, but the classic canned version imbues the cake with its nostalgic flavor.
Replace whole milk with coconut milk for a tropical variation.