Skillet Pineapple Upside Down Cake

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Let’s take a walk back in time ’cause I’m going all retro on you.




With a Skillet Pineapple Upside Down Cake.  What?  Rachelle, how positively 1920’s and 30’s of you!




With Mother’s Day this weekend I obviously thought of my mom and my daughter.  I also got to thinking about my grandmother.  She used to make a Skillet Pineapple Upside Down Cake to beat the band.




I’ve told some of you before how I inherited her recipe box.  Her dad made it by hand for her when she married my Pap.




Can you see the date?  December 23, 1932.  Holy cannoli that was a long time ago.  I searched all through the box for the recipe and sadly it wasn’t there.  So I put my dear friend Google to work and hijacked this recipe because this cake had to happen.




Pretty much all Pineapple Upside Down Cakes start the same.  Melt butter in a cast iron skillet, stir in some brown sugar, arrange pineapple slices and pop in some cherries.  You can totally do it this way.




Or you could be ridiculous like me and put cherries in every possible available space.




I’m just sayin’




Happy Mommy’s Day Y’all!


Skillet Pineapple Upside Down Cake


  • 1 stick butter
  • 1 1/4 cup brown sugar
  • 1 can of sliced pineapple, drained and 2/3 cup juice reserved
  • 9 - 25 maraschino cherries
  • 4 eggs, separated
  • 1 1/2 cup sugar
  • 1 1/2 cup flour
  • 1/2 teaspoon salt
  • 1 teaspoon baking powder


  1. Preheat oven to 325
  2. In a cast iron skillet, melt butter over medium-low heat, stir in brown sugar, and spread in an even layer over the bottom of the skillet
  3. Arrange pineapple slices around outside of the skillet in a circle and set one in the middle
  4. Add a cherry to the center of each pineapple - you can stop here or toss more cherries in every available space - set aside
  5. In a saucepan, heat pineapple juice on low until warm
  6. Beat egg yolks on medium until thick and bright yellow, slowly add sugar while beating
  7. Slowly add warm pineapple juice, mixing until combined
  8. Combine flour, salt, and baking powder
  9. Reduce mixer speed to low and slowly add dry ingredients until incorporated, transfer to a large mixing bowl
  10. Clean mixing bowl and whisk thoroughly and dry completely
  11. Beat egg whites on medium until stiff peaks form - about 10 minutes
  12. Fold egg whites into the batter until fully incorporated
  13. Pout batter in the skillet over pineapples and spread evenly
  14. Bake at 325 for 45 - 50 minutes
  15. Cool 30 minutes then invert onto a platter
  16. Serve with whipped cream or ice cream
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Adapted slightly from My Mother’s Southern Desserts by James and Martha Pearl Villas (William Morrow Cookbooks, 1998) republished in Southern Living and


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30 Responses to Skillet Pineapple Upside Down Cake

  1. Rachelle, this cake conjures up all sorts of memories! Totally makes me think of my grandmother as well! Your version looks terrific and I simply love that you used the cherries in excess. I mean why not?!? 🙂 The recipe box you inherited is beautiful! That’s soo neat, now you can add your recipes and pass it down and one day it will have generations of recipes. Thats seriously one of the coolest things ever. Love. It! Thanks for sharing, chicke! Cheers♡

    • That’s awesome, Cheyanne! I’m so glad this cake reminds you of your grandmother too. What can I say? I’m kind of ridiculous when it comes to cherries. I love that recipe box and am very lucky to have it. Cheers!

  2. Gram would be so happy if she knew your were sharing recipes and her very one recipe box. Handing it down to you was meant to be. You are the only one in the family who totally enjoys what you do. That old black skillet was the “home” of the famous Pineapple Upside Down Cake.
    A perfect time to share. Happy Mother’s Day!

  3. By the way, she didn’t have a recipe. That’s what you inherited from her…………throw it all together. I’m envious.

  4. Love that you inherited that recipe box! Talk about a family treasure and how wonderful that you share her love of cooking and baking even two generations later 🙂 This cake looks delicious and I LOVE that it’s made in a skillet!

    • Thanks Medha. It’s a total treasure! Every time I look through that box I think of my Gram. Sometimes I just want to look through just to feel close to her. I miss her every day. 🙂

  5. Oh my god, my ultimate favorite cake! I made it 10 times in 1 month during my trip to India last year..haha..everyone was obsessed with it I guess. This looks perfect and you made it in a skillet! Now pass me a BIG slice please!

  6. Oh yumm! That cake looks to-die-for delicious, Rachelle! Perfect for Mother’s day! and for me, any day of the year! I can have a big slice with tea, right now 🙂

  7. What a sweet story. I love reading about family traditions and recipes. This reminds me of the pineapple upside down cake that my mom used to make. I need to try and make a vegan one this summer because this looks fantastic!

    • I love that this reminded you of your mom’s cake, Linda! Could you whip some coconut cream to use instead of the eggs? Those are the only non-vegan ingredients, right? Maybe it would give it a bit of a Pina Colada flair! Hmmmmm – maybe we are on to something here!

    • Thanks Kathy! I treasure it and it sits in a very special place in my kitchen where I can see it every day!

  8. I’m a huge fan of retro. I’m also a huge fan of old recipe files and books. They yield the best recipes! And this cake is perfect. Love how you mashed all the cherries in there that you could!

    • Thanks Mir! I’m totally nostalgic over here and you can never have too many cherries!

    • It was sticky, Dani! I’m sorry it’s freezing for you right now – we went straight from winter to summer here in the Carolinas!

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