3 amazing retro pineapple upside-down cake recipes

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Pineapple Upside Down Cake

Note: This article may feature affiliate links to Amazon or other companies, and purchases made via these links may earn us a small commission at no additional cost to you. Find out more here.

If you love the tangy taste of pineapple, and have been hoping to find some delicious old-fashioned pineapple upside-down cake recipes, you just need to look back a few decades!

We have three tasty classic tropical dessert recipes here for you from the olden days.

Homemade pineapple upside-down cake

#1. Double pineapple upside-down cake retro recipe (1953)

There’s no mystery why pineapple upside-down cake is such a popular dessert. The refreshing, fruity flavor permeates the tender cake, and the pineapple turns an irresistible, glistening amber color from baking in the brown sugar.

In addition, 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.

For the topping, cut pineapple slices in half and arrange spoke-fashion or in a zigzag pattern. Or, if you prefer pineapple tidbits or chunks, they are attractive in a petal design.

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

Crushed pineapple can also be used by spreading it evenly over the brown sugar. Walnut halves, cherries, pitted dates or prunes, or a lacy border of shredded coconut can add the extra touch of garnish.

This special recipe 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.

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.

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

Ingredients

  • 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 water
  • 1/2 teaspoon vanilla

Instructions

  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 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.


#2. Vintage pineapple upside-down cake recipe (1975)

ALSO TRY: Dole’s crushed pineapple upside-down bundt cake recipe (1970)

Pineapple Upside Down Cake

Pineapple upside-down cake (1975)

Yield: 8
Prep Time: 20 minutes
Cook Time: 50 minutes
Additional Time: 10 minutes
Total Time: 1 hour 20 minutes

Ingredients

  • 1 cup sugar
  • 3 tablespoons cornstarch
  • 1 can (no. 303) crushed pineapple
  • 2 tablespoons melted butter
  • 1/2 cup maraschino cherries
  • 1-2/3 cup all purpose flour
  • 1/2 teaspoon salt
  • 2-1/4 teaspoons baking powder
  • 1/3 shortening
  • 2 eggs, beaten
  • 1/2 teaspoon vanilla
  • 1/2 cup milk

Instructions

  1. Mix 1/3 cup of the sugar with the corn starch, add juice drained from the pineapple.
  2. Cook in heavy 10-inch skillet over direct heat stirring constantly until sauce boils and becomes clear.
  3. Add drained pineapple and butter.
  4. Drain cherries thoroughly and arrange in a pattern in the pineapple mixture.
  5. Sift flour; measure and re-sift 3 times with salt and baking powder.
  6. Cream the 1/3 cup shortening until soft.
  7. Add the remaining 2/3 cups sugar and the eggs.
  8. Beat vigorously until smooth and fluffy.
  9. Stir in vanilla.
  10. Add flour mixture and milk alternately, beginning and ending with flour and beating well after each addition.
  11. Turn batter into skillet over pineapple.
  12. Bake in moderate oven at 350 (F) for 35 to 40 minutes or until center of cake is springy when lightly pressed with fingertips.
  13. Cool in pan or rack for about 10 minutes; then turn out on serving plate.
  14. Serve warm with or without whipped cream.

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As an Amazon Associate and member of other affiliate programs, qualifying purchases made via our links earns us a small commission at no additional cost to you.

Nutrition Information:
Yield: 8 Serving Size: 1
Amount Per Serving: Calories: 534Total Fat: 6gSaturated Fat: 3gTrans Fat: 0gUnsaturated Fat: 2gCholesterol: 56mgSodium: 427mgCarbohydrates: 108gFiber: 3gSugar: 32gProtein: 12g

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.


#3. Waikiki pineapple upside-down cake (1975)

SEE MORE: Hawaii travel in the ’70s: Look back at Honolulu & Waikiki

Pineapple Upside Down Cake and cup of coffee on white wooden tab
Photo by Mark_KA/Deposit Photos

Pineapple Upside Down Cake and cup of coffee on white wooden tab

Waikiki pineapple upside-down cake (1975)

Yield: 8
Prep Time: 20 minutes
Cook Time: 35 minutes
Total Time: 55 minutes

Ingredients

  • 2 tablespoons butter or margarine
  • 1/4 cup brown sugar (packed)
  • 8-1/2 ounces sliced pineapple, drained
  • 1-1/2 cups buttermilk baking mix
  • 1/2 cup granulated sugar
  • 1 egg
  • 1/2 cup milk or water
  • 2 tablespoons shortening
  • 1 teaspoon vanilla
  • 1/2 cup coconut

Instructions

  1. Melt butter in oven in square pan (8- by 8- by 2-inches) or round layer pan (9-1/2- by 1-1/2-inches).
  2. Sprinkle with brown sugar and arrange pineapple slices over the brown sugar.
  3. Blend remaining baking mix, sugar, egg, milk or water, shortening and vanilla.
  4. Add coconut.
  5. Mix on low speed for about 1/2 minute.
  6. Scrape bowl frequently.
  7. Beat for 4 minutes at medium speed.
  8. Pour batter over butter mixture and pineapple slices.
  9. Bake for 30 to 35 minutes or until wooden pick inserted in center comes out clean.
  10. Invert to heat-proof plate. Serve warm.

Recommended Products

As an Amazon Associate and member of other affiliate programs, qualifying purchases made via our links earns us a small commission at no additional cost to you.

Nutrition Information:
Yield: 8 Serving Size: 1
Amount Per Serving: Calories: 263Total Fat: 11gSaturated Fat: 6gTrans Fat: 0gUnsaturated Fat: 5gCholesterol: 37mgSodium: 378mgCarbohydrates: 36gFiber: 1gSugar: 26gProtein: 5g

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.

NOW SEE THIS: Weird retro ways to serve pineapple (and a few good ideas, too)

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