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Home » Recipes » Sweets, Treats & Desserts » Cakes » Old-Fashioned Pineapple Upside Down Cake

Old-Fashioned Pineapple Upside Down Cake

You’ll love this pineapple upside down cake using crushed pineapple. Not only is it delicious, but it is much easier to serve than using the slices.


How to make good old-fashioned Pineapple Upside Down Cake from Cosmopolitan Cornbread

This cake has been my favorite cake of all time since I was a kid. I often requested this for my birthday, and now-a-days my daughter does the honors when it rolls around.

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To begin, preheat your oven to 350 degrees.

In a 10 inch cast iron skillet, melt 1/3 cup of butter over very low heat.

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Meanwhile, drain a 14 ounce can of crushed pineapple. Press the excess juice from the pineapple as well. You want this as dry as possible. Set aside.

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In a bowl, combine 1 1/3 cup all-purpose flour, 2 teaspoon baking powder and 1/2 teaspoon salt. Stir together and set aside.

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When the butter is melted, add in 1/2 cup brown sugar. Stir it together to dissolve, and remove it from the heat.

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In your mixing bowl, beat together 1/3 cup shortening and 1 cup sugar until creamed together. Beat in 2 eggs.

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Mix in half of your dry ingredients.

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Mix in 2/3 cup milk

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Mix in the remaining dry ingredients, and finally add in 1 1/2 teaspoon vanilla.

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Grab your pineapple and spread it over the bottom of the skillet with the butter and brown sugar.

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Gently spread the batter over pineapple.

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Bake this for 40-50 minutes or until it tests done with a toothpick. Allow it to rest in the skillet for a couple minutes, then turn it out onto your platter.

I love this part…the little bits of pineapple that OOPS! Get left in the pan. Let me take care of this real quick!

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Cool the cake completely.

How to make good old-fashioned Pineapple Upside Down Cake from Cosmopolitan Cornbread

Enjoy!

How to make good old-fashioned Pineapple Upside Down Cake from Cosmopolitan Cornbread

Did you make and enjoy this recipe from Cosmopolitan Cornbread? Please rate it below and leave a comment to share your thoughts! 

Yield: 8

Old-Fashioned Pineapple Upside Down Cake

How to make good old-fashioned Pineapple Upside Down Cake from Cosmopolitan Cornbread

You'll love this pineapple upside down cake using crushed pineapple. Not only is it delicious, but it is much easier to serve than using the slices.

Prep Time 10 minutes
Cook Time 1 hour
Total Time 1 hour 10 minutes

Ingredients

  • 1/3 c butter
  • 1/2 c brown sugar
  • 14 oz. crushed pineapple
  • 1 1/3 c all-purpose flour
  • 2 tsp baking powder
  • 1/2 tsp salt
  • 1/3 c shortening
  • 1 c sugar
  • 2 eggs
  • 2/3 c milk
  • 1 1/2 tsp vanilla

Instructions

  1. To begin, preheat your oven to 350 degrees.
  2. In a 10 inch cast iron skillet, melt the butter over very low heat.
  3. Meanwhile stir the flour, baking powder and salt together in a bowl. Set aside.
  4. To the melted butter, add the brown sugar. Stir together and let the brown sugar dissolve.
  5. Remove from heat.
  6. In a mixing bowl, beat together the shortening and sugar until creamy.
  7. Add in the eggs, and mix well.
  8. Mix in half of your dry ingredients. Then add in the milk, and finally the remaining dry ingredients.
  9. Stir in the vanilla. Beat for just a minute until smooth.
  10. Press any excess liquid from the pineapple and then spread the pineapple over the bottom of the skillet.
  11. Gently pour the batter over the top and smooth the top.
  12. Bake for 40-50 minutes or until it tests done with a toothpick.
  13. Allow it to cool a couple minutes in the skillet, then turn it out onto a platter.
  14. Cool completely, and enjoy!

Notes

If you do not have a cast iron skillet, this can be made in a round cake pan. Simply melt the butter before adding it to the pan. Do the same from there.

Nutrition Information:

Yield:

8

Serving Size:

1

Amount Per Serving: Calories: 419Total Fat: 18gSaturated Fat: 9gTrans Fat: 0gUnsaturated Fat: 8gCholesterol: 73mgSodium: 360mgCarbohydrates: 61gFiber: 1gSugar: 43gProtein: 5g

This data was estimated and provided by Nutritionix. Accuracy not guaranteed.

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37 thoughts on “Old-Fashioned Pineapple Upside Down Cake”

  1. This was simply Wonderful, I have made my second one, it is so good! Thank you for the recipe and I love it with the crushes pineapple. I also love the gooey edges!😋

    Reply
  2. So delicious! I used a fresh pineapple and my 10” cast iron skillet. Thank you! I posted photos and recipe link to The Blue Willow Pantry Facebook page😊

    Reply
  3. I made this today, but cut the recipe in half so that I could bake it in my Ninja Foodi. I also used Featherweight no sodium baking powder and added nearly 1/2 cup of sour cream. I also used oat milk and organic coconut oil. I added @ 15 chopped raspberries to the brown sugar/butter mixture. Thank you so much for giving me a recipe I could actually use in my Foodi! It is light, fluffy and delicious!

    Reply
  4. Hello Diana! I looked back over and saw what you were talking about with the missing line of instructions. Thankfully it was correct in the printable version, but I have made that correction. I hope the cake turned out great for you! Let me know how the substitution of the butter for the shortening worked out.

    Reply
  5. Pineapple Upside Down Cake is my #1 favorite cake too! We make it for Christmas dinner dessert & I make it for special occasions! I use pineapple rings, but I might use crushed next time so I can pick up the bits like you! Mmmm

    Reply
  6. Pineapple upside down cake has got to be one of the best old fashioned cakes. It look amazing Constance, and so lucky to have someone bake it for you!
    My recent post Ice Cream Granola Truffles #LaborDay #SundaySupper

    Reply
  7. Hey, at least you used a fork for the pineapple bits. I'd just get in there with my fingers.
    My recent post Red, White & Blue Greek Yogurt Cheesecake Dip Trio for #SundaySupper #LaborDay

    Reply
  8. I love the idea of a pineapple upside down cake made with crushed pineapple! This is one of my dad's favorite cakes!

    Reply
  9. I've never seen a pineapple upside down cake baked in an iron skillet. You are so clever, Constance! Thanks to you I've got another scrumptious to-do in my newly acquired iron skillet =)

    Reply

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