Home » Pineapple Upside Down Cake: From the 1920s

Pineapple Upside Down Cake: From the 1920s

People have been baking Pineapple Upside Down Cake for over 100 years, and it’s still just as good today as it ever was. This classic no-fuss recipe uses wholesome ingredients and no fancy baking skills are required!

Pineapple Upside Down Cake on a black cake pan.

I love Pineapple Upside Down Cake. It was one of my grandmother’s favorite cakes, and she’d make it for just about every special event and family gathering. 

It’s such a simple cake to make. All you need is a can of pineapple, some maraschino cherries, and some staple pantry supplies. That’s it! 

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Take a trip down memory lane and bake this cake today. I know you’ll love it as much as I do!

A Pineapple Upside Down Cake on a black cake pan.

History

The Pineapple Upside Down Cake soared in popularity in the 1920s following the commercial availability of canned pineapple, courtesy of the Dole Pineapple Company. This accessibility transformed an exotic treat into a household staple. During the economic challenges of the Great Depression, the cake symbolized American innovation and culinary flair, providing a delightful mix of flavor and beauty. 

Ingredients

  • Butter – Salted.
  • Brown sugar
  • Canned pineapple
  • Maraschino cherries – About 16 cherries.
  • Flour
  • Baking powder
  • Pineapple juice
  • Vanilla extract
  • Eggs
  • Granulated sugar
Pineapple Upside Down Cake ingredients with label.

How To Make Pineapple Upside Down Cake

  1. Preheat your oven to 350°F (175°C).
  2. Melt the butter in the cake pan by popping the pan into the oven for a few minutes to melt, then spread it around.
  3. Sprinkle the brown sugar on top.
  4. Arrange the pineapple slices over the sugar layer, placing a maraschino cherry in the center of each pineapple slice and any spaces in between.
  5. Combine the flour and baking powder in a medium-sized bowl. Set this mixture aside for later.
  6. Whip the eggs on high speed until they are thick and fluffy, about 5-6 minutes, in a stand mixer or using a handheld mixer.
  7. Slowly incorporate the granulated sugar into the eggs, ensuring it mixes thoroughly after each addition.
  8. Blend in the reserved pineapple juice and vanilla extract.
  9. Gradually mix the dry ingredients into the wet mixture until they are just combined, taking care not to overmix.
  10. Gently pour the batter over the arranged fruit in the pan, smoothing it out to an even layer.
  11. Place the cake in the oven and bake for 30-40 minutes, or until a toothpick inserted in the center comes out clean.
  12. Let the cake cool in the pan for 10 minutes after baking. Loosen the edges with a knife, then invert the cake onto a serving plate by flipping the pan over.
  13. Enjoy your beautifully crafted dessert!

Step-By-Step Process

Chef Jenn’s Tips

  • Ensure the butter and sugar mixture is thoroughly melted and spread to avoid the cake sticking to the pan.
  • A toothpick should come out clean or with just a few crumbs to indicate the cake is perfectly baked.
  • Let the cake rest in the pan for 10 minutes before inverting to allow it to set properly and release cleanly.

Recommended

Serving suggestions

This vintage Pineapple Upside Down Cake recipe is the perfect finish to just about any meal. From special occasion dinners like Grandmother used to serve to potlucks and BBQs, it’s versatile and easy enough to make any day of the week!

Top-down shot of Pineapple Upside Down Cake beside pineapple.

Storage

Keep any leftovers in an airtight container at room temperature for up to 2 days or refrigerate for up to 5 days. For long-term storage, wrap the cake well in plastic and foil, then freeze for up to 3 months. Thaw overnight in the refrigerator before serving.

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Pineapple Upside Down Cake on a black cake pan.

Pineapple Upside Down Cake

Chef Jenn
Easy, delicious, and so stunning, this vintage Pineapple Upside Down Cake recipe is just as good as it was nearly 100 years ago!
5 from 1 vote
Prep Time 10 minutes
Cook Time 30 minutes
Total Time 40 minutes
Course Dessert
Cuisine American
Servings 8 servings
Calories 250 kcal

Ingredients
  

  • 3 tablespoons butter salted
  • ½ cup packed brown sugar
  • 1 16 oz can canned pineapple rings drained but 1/3 cup juice reserved
  • 16 maraschino cherries about 16 cherries
  • 1 cup flour
  • ½ teaspoon baking powder
  • cup pineapple juice
  • 1 teaspoon vanilla extract
  • 2 eggs
  • cup granulated sugar

Instructions
 

  • Preheat your oven to 350°F (175°C).
  • Melt the butter in the cake pan by popping the pan into the oven for a few minutes to melt, then spread it around.
  • Sprinkle the brown sugar on top.
  • Arrange the pineapple slices over the sugar layer, placing a maraschino cherry in the center of each pineapple slice and any spaces in between.
  • Combine the flour and baking powder in a medium-sized bowl. Set this mixture aside for later.
  • Whip the eggs on high speed until they are thick and fluffy, about 5-6 minutes, in a stand mixer or using a handheld mixer.
  • Slowly incorporate the granulated sugar into the eggs, ensuring it mixes thoroughly after each addition.
  • Blend in the reserved pineapple juice and vanilla extract.
  • Gradually mix the dry ingredients into the wet mixture until they are just combined, taking care not to overmix.
  • Gently pour the batter over the arranged fruit in the pan, smoothing it out to an even layer.
  • Place the cake in the oven and bake for 30-40 minutes, or until a toothpick inserted in the center comes out clean.
  • Let the cake cool in the pan for 10 minutes after baking. Loosen the edges with a knife, then invert the cake onto a serving plate by flipping the pan over.
  • Enjoy your beautifully crafted dessert!

Notes

Chef Jenn’s Tips

  • Ensure the butter and sugar mixture is thoroughly melted and spread to avoid the cake sticking to the pan.
  • A toothpick should come out clean or with just a few crumbs to indicate the cake is perfectly baked.
  • Let the cake rest in the pan for 10 minutes before inverting to allow it to set properly and release cleanly.

Nutrition

Serving: 1sliceCalories: 250kcalCarbohydrates: 48gProtein: 3gFat: 6gSaturated Fat: 3gPolyunsaturated Fat: 0.4gMonounsaturated Fat: 2gTrans Fat: 0.2gCholesterol: 52mgSodium: 81mgPotassium: 68mgFiber: 1gSugar: 35gVitamin A: 196IUVitamin C: 1mgCalcium: 43mgIron: 1mg
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