2 1/2 cups all-purpose flour
3 teaspoons baking powder
2 cups granulated sugar
1 stick chilled butter, divided
1/4 cup shortening
1 1/2 cups milk
2 large eggs
2 teaspoons pure vanilla extract
1-20 oz. can sliced pineapple, 2 tablespoons juice reserved
1 1/3 cups packed brown sugar
Preheat the oven to 350°F. Combine the flour, baking powder, salt, sugar, 1/2 stick butter, shortening, milk, eggs, vanilla, and two tablespoons pineapple juice. Stir until combined.
Melt the remaining butter in a cast iron skillet over medium heat. Swirl melted butter to thoroughly coat the skillet. Sprinkle the brown sugar over the butter. Evenly coat the skillet with the sugar and make sure the entire skillet is covered. As soon as the sugar dissolves, place a layer of pineapple over the top. Place a cherry in the center of each pineapple. Pour the batter over the top of the pineapple slices.
Bake the cake for 30-40 minutes until a toothpick inserted in the center comes out clean. Run a knife around the edge of the cake then place a cake plate upside down on top of the skillet. Very carefully invert the skillet so that the cake is turned upside down onto the cake plate. Allow the cake to cool slightly before serving.
Based on a recipe from The Pioneer Woman Cooks: Recipes from an Accidental Country Girl.