Recipes » Dessert Recipes » Skillet Pineapple Upside Down Cake

Skillet Pineapple Upside Down Cake

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The iconic Skillet Pineapple Upside Down Cake with sweet pineapple slices caramelized in butter and brown sugar topped with a fluffy yellow cake batter.
5 from 7 votes
Prep Time 20 minutes
Cook Time 50 minutes
A slice of pineapple upside down cake on a serving plate.

The iconic Skillet Pineapple Upside Down Cake with sweet pineapple slices caramelized in butter and brown sugar topped with a fluffy yellow cake batter. Serve one for an old-fashioned trip down memory lane.

I know I don’t have to tell you all how much I enjoy a nostalgic, warm feeling recipe. I’m talking about recipes like this Skillet Pineapple Upside Down Cake. Now, I ask you, what could be more nostalgic than that? Not to mention delicious.

A slice of pineapple upside down cake on a serving plate.

Sweet pineapple slices caramelized with butter and brown sugar topped with a fluffy yellow cake batter. Yum. Just yum.

I like mine served warm and unadorned. Others like theirs topped with a bit of sweetened whipped cream or a scoop of vanilla ice cream.

The supposed first mention of Pineapple Upside Down Cake is reported in “Fashionable Food: Seven Decades of Food Fads (1995),” in which Sylvia Lovegren traces the recipe to a 1924 Seattle fund-raising cookbook…”While rooting around in old women’s magazines I found a Gold Medal Flour ad with a full-page, four-color picture of Pineapple Upside-Down Cake–a round cake with six slices of pineapple, candied red cherries, and a brown sugar glaze.”

The classic Pineapple Upside Down Cake was not, of course, the first cake baked bottom side up. Other upside down preparations include the French Tarte Tatin and the Brazilian Bolo de Banana. I’ve made Tarte Tatin but have never tried the Bolo de Banana. It’s on my list to make soon!!

In the meantime, let’s take a stroll down memory lane and enjoy this delicious vintage recipe!

About the Ingredients

  • Light Brown Sugar – when measuring brown sugar, make sure to pack it into the measuring cup for an accurate measure.
  • Canned Pineapple Slices – to be true to the original, old fashioned recipe, you’ll need canned, round slices of pineapple.
  • Maraschino Cherries – another ingredient used in the original recipe, but optional if you don’t like them.
  • Whipped Cream or Vanilla Ice Cream – not absolutely necessary, but really good on top!

You’ll find detailed measurements for all ingredients in the printable version of the recipe at the bottom of this post.

How to Make Pineapple Upside Down Cake

Let’s Go Step-by-Step

I always like to show you the photos and step-by-step instructions for my recipes to help you picture how to make them in your own kitchen. If you just want to print out a copy, you can skip to the bottom of the post where you’ll find the recipe card.

Make the Pineapple and Sugar Layers

Preheat the oven to 325 degrees.

  • Melt the butter over medium-low heat in a 10” cast iron skillet.
  • Remove the skillet from the heat and spread the brown sugar evenly over the melted butter in the bottom of the pan. 
  • Drain the pineapple reserving 1/4 cup of the juice. Arrange the pineapple rings in a single layer on top of the brown sugar in the skillet.
  • Place a maraschino cherry in the center of each slice.

Mix the Cake Batter

  • Beat the egg yolks in a medium bowl until light yellow and thickened.
  • Gradually beat in the sugar.
  • Slowly add the reserved pineapple juice to the yolk mixture, beating well.
  • With the mixer on slow speed, slowly add the flour, salt, and baking powder to the egg yolk mixture, until blended.
  • In a separate bowl, beat the egg whites until stiff peaks form.
  • Fold the egg whites into the egg yolk and flour mixture.

Spoon Batter over Pineapple Slices

Spoon the batter over the pineapple slices and cherries in the skillet.

Bake

Bake for 40-50 minutes or until a skewer or toothpick inserted near the center comes out clean. Cool the cake in the skillet for 30 minutes. Invert onto a serving plate. 

Completed pineapple upside down cake on a wooden board with a serving on a plate in the forefront.

Serve

May be served warm or cool with whipped cream or ice cream if desired.

Storage

Pineapple Upside Down Cake can be left out at room temperature for at least 24 hours. After that, it’s best stored in the refrigerator. It’s easiest to wrap the cake and serving plate together in plastic wrap. then store it in the refrigerator for up to three days. I think this cake is best served warm or at room temperature.

To freeze – allow the cake to cool completely. Wrap tightly in plastic wrap followed by aluminum foil. Place the wrapped cake in a zip top bag and freeze for up to three months. To serve, allow the cake to thaw overnight in the refrigerator. It can be rewarmed in a low oven.

FAQs

What is the best way to remove an upside down cake from the pan?

To remove an upside down cake from the pan, first let it cool on a wire rack for 15 to 30 minutes. After cooling, run a knife or spatula between the cake and pan. Then, using a serving plate that is larger all around than the pan, place the plate upside down on top of the pan. Grasp the pan and plate with both hands and invert the whole thing (be sure to use oven mitts if the pan is still hot). Sit the plate down and carefully lift the pan leaving the inverted cake on the serving plate.

What’s the point of “upside down” cakes anyway?

The technique of baking cakes upside down, originated centuries ago before it was common for individual homes to have ovens. Cakes were cooked on top of the heat source in a single pan with the toppings on the bottom of the pan. After cooking, the cake was flipped so that the toppings were then on top.

I don’t have a cast iron skillet. What can I substitute?

If you don’t have a cast iron skillet, you can easily substitute a standard 9-inch cake pan or square baking pan.

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Recipe

A slice of pineapple upside down cake on a serving plate.

Pineapple Upside Down Cake

The iconic Skillet Pineapple Upside Down Cake with sweet pineapple slices caramelized in butter and brown sugar topped with a fluffy yellow cake batter.
5 from 7 votes
Print It Rate It Save Text It
Course: Desserts
Cuisine: American
Prep Time: 20 minutes
Cook Time: 50 minutes
Total Time: 1 hour 10 minutes
Servings: 8 servings
Calories: 293kcal
Author: Lana Stuart

Ingredients

  • ¼ cup butter
  • cup firmly packed light brown sugar
  • 16 ounces canned pineapple slices
  • 7 maraschino cherries
  • 2 large eggs separated
  • ¾ cup granulated sugar
  • ¾ cup all-purpose flour
  • teaspoon salt
  • ½ teaspoon baking powder
  • Whipped cream or vanilla ice cream optional

Instructions

  • Preheat the oven to 325 degrees.
  • Melt the butter over medium-low heat in a 10” cast iron skillet. Remove from heat and spread the brown sugar evenly over the bottom of the skillet.
  • Drain the pineapple reserving 1/4 cup of the juice. Arrange pineapple slices in a single layer on top of the brown sugar. Place a maraschino cherry in the center of each slice.
  • Beat the egg yolks in a medium bowl until light yellow and thickened. Gradually beat in the sugar. Gradually add the reserved juice to the yolk mixture, beating well.
  • With the mixer on slow speed, slowly add the flour, salt, and baking powder to the egg yolk mixture, until blended.
  • In a separate bowl, beat the egg whites until stiff peaks form. Fold the egg whites into the egg yolk and flour mixture. Spoon batter over pineapple slices.
  • Bake for 40-50 minutes or until a skewer inserted near the center comes out clean. Cool cake in skillet for 30 minutes. Invert onto a serving plate.
  • May be served warm or cold with whipped cream or ice cream if desired.

Notes

Storage:
This dessert can be left out at room temperature for at least 24 hours. After that, it’s best stored in the refrigerator. It’s easiest to wrap the cake and serving plate together in plastic wrap. then store it in the refrigerator for up to three days. To freeze – allow the cake to cool completely. Wrap tightly in plastic wrap followed by aluminum foil. Place the wrapped cake in a zip top bag and freeze for up to three months. To serve, allow the cake to thaw overnight in the refrigerator. It can be rewarmed in a low oven.
  • To remove the cake from the pan, first let it cool on a wire rack for 15 to 30 minutes. After cooling, run a knife or spatula between the cake and pan. Then, using a serving plate that is larger all around than the pan, place the plate upside down on top of the pan. Grasp the pan and plate with both hands and invert the whole thing (be sure to use oven mitts if the pan is still hot). Sit the plate down and carefully lift the pan.
  • If you don’t have a cast iron skillet, you can easily substitute a standard 9-inch cake pan or square baking pan.

Nutrition Information

Serving: 1 | Calories: 293kcal | Carbohydrates: 56g | Protein: 3g | Fat: 7g | Saturated Fat: 4g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 2g | Trans Fat: 1g | Cholesterol: 56mg | Sodium: 135mg | Potassium: 125mg | Fiber: 1g | Sugar: 46g | Vitamin A: 267IU | Vitamin C: 5mg | Calcium: 51mg | Iron: 1mg

Nutrition information is calculated by software based on the ingredients in each recipe. It is an estimate only and is provided for informational purposes. You should consult your health care provider or a registered dietitian if precise nutrition calculations are needed for health reasons.

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— This post was originally published on January 26, 2016. It has been updated with new photos and additional information.

Skillet Pineapple Upside Down Cake on a serving plate.

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22 Comments

  1. When I was a kid, I used to love pineapple upside down cake. But honestly the versions I knew then were from a grocery or baker. Your version looks spectacular and makes me want to run and grab my cast iron skillet right now. Thanks for the food history lesson too – always appreciate knowing the background of a recipe, especially a vintage recipe as venerable as this one.

  2. One of my all- time favorites! My mother in law almost always makes this for my birthday. Thanks for hosting and all of the comfort food inspiration! You know you are one of my favorite cooks Lana!

  3. I was happy to see you choose this cake Lana or I might have done it. Pineapple Upside Down Cake and German Chocolate Cake are simply my two most favorite cakes EVER. I might add rum to both. :)

    Thanks for hosting this month; this theme brought out the best in everyone!

  4. It seems that also here in Italy we had the same upsidedown pineapple cake!! I remeber that my Grandmother used to prepare it , and she also decorated it with cherries! It’s a pleasant memory!
    thanx! Simona

    P.S.: is this Progressive Eat opened to other bloggers or is it only for your group?

  5. It’s one of my favorite cakes ever. I simply love how it tastes and how easy it is to make. Wish I could have a slice of your cake right now. So

  6. I have always loved pineapple upside down cake. I like to add well drained crushed pineapple to fill in the spaces between the pineapple rings. Just that much more to love!

    Miss P

  7. You can’t beat a good, simple cake like this. Thanks for the history lesson, too! I love finding out about where recipes came from.

    1. I like the history as well, Megan. The more you learn about classic and basic recipes, the more you realize that there’s not much really new or unique – it’s all variations on a theme :-)

  8. What a wonderful recipe – and perfect for this month’s theme. It definitely takes me back – it was always one of my favorite recipes. Thanks so much for sharing it with us, and thanks so much for a very fun theme for the this month. I spent a very enjoyable time remembering different foods from my childhood and early adulthood. Thank you :-)

  9. What a gorgeous Pineapple Upside Down Cake and how interesting to read the background of it all. This is my hubby’s favorite cake of all time, and I will bookmark your recipe to make it for him. Thanks for your patience with me, my tech issues, snow Jonas problems and all. Nice of you to host this event, you did a superb job. Fun doing Progressive Eats with you and the group, Lana. All the best!

    1. Thanks for so kindly volunteering at the last minute, Betty! I do hope you’ll make the cake and that your hubby enjoys it :-)

  10. You and Barb have hit on my dad’s two favorite desserts today! I remember my mom making the occasional pineapple upside down cake per his request. I always loved the cake just beneath the pineapple—so sweet and caramelly! Pure comfort! Thanks for suggesting this wonderful theme, Lana.

    1. Aw, I’m so glad we made your dad’s favorites! They’re two of my favorites as well. Glad you enjoyed working with the theme.

  11. One of my hands down favorites, Lana! I love-love-love this theme so much. What a great Progressive Eats round up! Thank you!