Pineapple Upside Down Cake for Bringing Back Retro Recipes #SundaySupper

We are getting retro at #SundaySupper. Immediately a Pineapple Upside Down Cake popped into my head. I went straight to my Better Homes and Gardens Dessert Cook Book that was published in 1960, I knew it had to be in there and I was right. I had never made one before but I now know why this cake was so hugely popular back in the 50’s and 60’s. It was around for much longer than that but those decades seem to be when everyone was making it. Dole started canning pineapple rings just after the turn of the century and pineapple replaced apples and cherries that had been popular until then. It has huge flavor and is so delicious. My little cake was gobbled right down.

With it’s ooey gooey caramel topping and the wonderful taste of pineapple, cherries and a little pecan, you can’t get anything better and it was so easy to make. I will be making this one again for sure!!

5.0 from 3 reviews
Pineapple Upside Down Cake for Retro Recipes Then and Now #SundaySupper
Recipe type: Dessert
Cuisine: American
Prep time: 
Cook time: 
Total time: 
Serves: 8
A delicious and easy cake that looks so impressive!
  • 3 Tbsp. butter
  • ⅔ cup brown sugar
  • 6 canned pineapple rings
  • 6 maraschino cheeries
  • 5 pecan halves
  • ⅓ cup shortening
  • ½ cup sugar
  • 1 egg
  • 1 tsp. vanilla
  • 1¼ cups cake flour
  • 1½ tsp. baking powder
  • ½ tsp. salt
  • ½ cup pineapple juice
  1. Preheat oven to 350F. Drain the pineapple reserving ½ cup of the juice.
  2. To make the topping melt the butter and pour it into a 9½" cake pan (you may want to spray this first with cooking spray, I didn't and my cake came out fine). Sprinkle in brown sugar and stir to combine. Arrange the pineapple slices, putting a cherry into the middle of each ring and a pecan half at the edge between each slice. Set aside.
  3. For the cake cream the shortening and sugar. Add the egg and vanilla and beat well until smooth and creamy. Whisk the dry ingredients together.Add the flour mixture alternatively with the pineapple juice and beat well after each addition scraping down the sides. Spread over the pineapple.
  4. Bake for 40-45 min. until golden and a cake tester comes out clean. Let cool 5 min. Run a knife around the edge of the cake and invert onto a cake platter. Serve warm with whipped cream or ice cream if desired or let cool completely.

Recipe adapted from Better Homes and Gardens Dessert Cook Book

Are you ready for more retro recipes? Take a look at what the talented Sunday Supper bloggers are sharing:

Sunday Supper Retro Appetizers:

Sunday Supper Retro Salads:

Sunday Supper Retro Breads and Sandwiches:

SundaySupper Main Dishes:

Sunday Supper Retro Sides and Veggies:

Sunday Supper Retro Desserts and Cocktails:

What fun to read the stories about the recipes! There’s lots of great food in the list. I admit I still make and enjoy many of them. Nice to see some updated versions too. Which one is your favorite?

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  1. says

    Talk of the retro Better Homes & Gardens recipes brings on the warm fuzzies. And your upside down pineapple cake is brilliant. It makes me want to bake one up for my own Sunday table!

  2. says

    Oh my goodness! I can’t tell you how many of these cakes I saw (and ate) at potlucks when I was growing up. Such a great recipe to share today.

  3. Jill says

    I love love love PAUSDC! If I have a can of opened coconut milk in the fridge I will use it instead of the juice to make it a pina colada upside down cake. Flaked coconut is nice in the cake too. (BTW do you know that you put the 1/2 cup PA juice into the topping section?)

  4. says

    My mom used to make this all the time, now my sister does. It is gooey and yummy. I had never made an upside down cake until recently, and glad I did. The kids loved it. And it’s so very easy. I’ve printed your recipe to try. Will let you know how it goes.

  5. says

    Oh, does this bring back memories! My mom would make this as a special treat for my dad. I’m heading to Iowa to see him for his 79th birthday next weekend, so I’ll check if he’d like this for his celebratory cake. I’ll use your recipe if the answer is yes :) THANKS!!!

  6. Helene Dsouza I Masala Herb says

    How pretty! I haven’t had pineapple upside down cake in ages. The first time I had it was in a friends house. It’s so not European, so it took me some time to discover this wonderful cake.

  7. says

    This looks fabulous, Tara! Pineapple upside down cake definitely comes to mind immediately when I think about retro foods. It’s still in style, in my opinion. You can’t go wrong with sugary, caramelized pineapple and a good vanilla cake.


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