- 1 20 ounce can Pineapple rings in heavy syrup
- 6 tablespoon butter
- 1 cup dark brown sugar
- 3/ 4 cup large maraschino cherries
- 3/ 4 cup reserved syrup from the pineapple
- 1/ 3 cup shortening
- 1/ 2 cup sugar
- 1 large egg
- 1 tsp pure vanilla extract
- 1 cup all-purpose flour
- 1 1/ 4 tsp baking powder
- 1/ 4 tsp salt
Pre-heat the oven to 350. Heat a 9" cast iron or non-stick skillet over medium-high heat. Add the butter and melt. Add the brown sugar and 1/4 cup of the reserved pineapple syrup. Stir until the sugar melts and the caramel starts to bubble.
Cook the caramel for 6-7 minutes then turn off the heat. Add the pineapple slices, covering the bottom of the skillet. Place one maraschino cherry in the center of each pineapple slice and place more maraschino cherries around the pineapple slices.
In a mixer bowl, cream together the shortening and sugar. Add the egg and vanilla and mix to combine. In a bowl, whisk together the flour, baking powder and salt, then add to the creamed mixture. Add the reserved 1/2 cup of pineapple syrup. Note: if the cake batter seems too thick, thin with water.
Spoon the batter over the top of the pineapple slices in the skillet. Smooth the top of the batter so that it seals over the pineapple and cherries. Bake the upside-down cake about 35 minutes or until the cake is set to the touch and browned.
Remove the skillet from the oven and place on a wire rack. Let the caramel slightly cool for 5 minutes before you turn the cake out. (Don't let the caramel cool too much or it will start to set hard and won't release from the skillet).
Place a rack on top of the cake, then gently invert the skillet, turning the cake "upside-down." The cake should gently release onto the rack, revealing the "top" of pineapple slices and maraschino cherries. Let cook about 15 minutes before serving.