Double pineapple upside-down cake recipe, step-by-step: A classic 1950s skillet dessert

Double pineapple upside-down cake classic recipe from the 1950s

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Vintage double pineapple upside-down cake recipe (1953)

There’s no mystery why pineapple upside-down cake is such a popular dessert: it’s because the refreshing, fruity flavor of the pineapple perfectly permeates the tender cake.

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.

Homemade double pineapple upside-down cake

ALSO TRY: 7 delicious old-fashioned pineapple pie recipes: Real classic ways to make this tropical dessert

How to make double pineapple upside-down cake

This is a flexible type of recipe. The cake part can be a plain white cake, sponge, chocolate, or even gingerbread. Or you can use a cake mix to save precious minutes.

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.

Walnut halves, cherries, pitted dates or prunes, or a lacy border of shredded coconut can add the extra touch of garnish.

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

double pineapple upside down cake ingredients

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.

double pineapple upside-down cake step 1

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!

double pineapple upside-down cake step 2

double pineapple upside-down cake step 3

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.

double pineapple upside-down cake step 4

double pineapple upside-down cake step 6

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.

double pineapple upside-down cake step 7

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.

This double pineapple upside-down cake is an easy and classic recipe

Homemade pineapple upside-down cake

Double pineapple upside-down cake (1953)

Yield: 8
Prep Time: 15 minutes
Cook Time: 55 minutes
Total Time: 1 hour 10 minutes


  • 2 cups crushed pineapple
  • 1/4 cup butter or margarine
  • 3/4 cup brown sugar
  • 1/4 cup shortening
  • 1/2 cup granulated sugar
  • 2 eggs, separated
  • 1-1/4 cups cake flour
  • 1 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1/4 cup milk or water
  • 1/2 teaspoon vanilla


  1. Measure 1/2 cup crushed pineapple without draining, and set aside to use in cake.
  2. Thoroughly drain remaining pineapple.
  3. Melt butter or margarine in 10-inch skillet and blend in brown sugar.
  4. Spread drained pineapple over evenly.
  5. Cream shortening with 1/4 cup of the granulated sugar.
  6. Sift flour, measure and sift again with baking powder, soda and salt; add to creamed mixture alternately with milk or water.
  7. Stir in vanilla and the 1/2 cup crushed, undrained pineapple.
  8. Beat egg whites until stiff and gradually beat in remaining 1/4 cup sugar.
  9. Fold into batter.
  10. Pour over pineapple in pan and bake in a moderate oven (350 degrees F) for 40 to 45 minutes.

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Nutrition Information:
Yield: 8 Serving Size: 1
Amount Per Serving: Calories: 526Total Fat: 14gSaturated Fat: 7gTrans Fat: 0gUnsaturated Fat: 6gCholesterol: 65mgSodium: 237mgCarbohydrates: 93gFiber: 2gSugar: 38gProtein: 8g

Click Americana offers approximate nutrition information as a general reference only, and we make no warranties regarding its accuracy. Please make any necessary calculations based on the actual ingredients used in your recipe, and consult with a qualified healthcare professional if you have dietary concerns.

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