Vintage double pineapple upside-down cake recipe (1953)
Depending on how you like it, you can cook this cake a little less for a fresher fruit flavor — but we also love it when the cake turns an irresistible, glistening amber color while baking, making the topping almost candy-like.
How to make double pineapple upside-down cake
This special recipe for double pineapple upside-down cake has crushed pineapple in both the topping and in the cake. However, if you wish to use the decorative pineapple rings on top, reserve two slices and cut them into small pieces to stir into the batter.
You could also cut the remaining pineapple slices in half and then arrange them spoke-fashion or in a zigzag pattern for added flair. If you prefer pineapple tidbits or chunks, they are attractive in a petal design.
The topping in this recipe is rather chewy and sugary, and if you wish one that is softer and makes into the cake a little, then add three tablespoons of milk to the butter and sugar mixture.
Ingredients for double pineapple upside-down cake
Clockwise from upper left: milk, vanilla, baking powder, baking soda, shortening, cake flour, sliced & crushed pineapple, eggs, sugar, melted butter and maraschino cherries
Step 1: Prepare the caramel-y topping
Melt butter or margarine in 10-inch cast iron skillet (or other oven-proof skillet) and blend in the brown sugar.
Step 2: Embellish the cake topping
Evenly spread the drained pineapple. Although the recipe originally requires only a crushed pineapple topping, we opted to include an additional layer of pineapple to achieve the classic look of pineapple upside-down cake with sliced pineapple and a pretty maraschino cherry grid. The choice is entirely yours!
Step 3: Make the cake batter
Start by creaming the shortening with the granulated sugar. Once that’s done, sift the flour, then measure it and sift it again. This time, however, add baking powder, soda, and salt to the sifting. Gradually combine this mixture with the creamed shortening and sugar, alternating with milk or water.
Next, mix in the vanilla along with half a cup of crushed pineapple (and no need to drain it).
Now it’s time to whip the egg whites until they’re stiff. As you’re doing this, gradually incorporate the remaining quarter cup of sugar.
The final step is to gently fold this fluffy egg white and sugar mixture into your batter.
Step 4: Bake the cake!
Next, pour the batter over the pineapple in the pan. Then, place the pan into a preheated oven at 350 degrees Fahrenheit. Let it bake for about 40 to 45 minutes.
Step 5: Cool and serve
Once it’s done baking, let the pan cool either in the pan or on a rack for about 10 minutes. After that, you can go ahead and turn it out onto a serving plate and serve warm.