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Pineapple Upside Down Cake

Pineapple Upside Cake from Judy Wear

This retro recipe for the ever-popular Pineapple Upside Down Cake was sent in by Judy Wear, who follows The Daily Doo Wop on Facebook. (Thank you, Judy Wear!) She writes that this was her mother’s recipe. Her Mom made it often because they always had company on Sundays after church. Her mother would make the cake on Saturday night. If they were having many people over, then she would make two cakes.

Cooking a cake with sliced fruits upside down in a pan or skillet has origins in the middle ages. Canned pineapple came about in 1901, and sliced pineapple in cans became available in the 1920s when an engineer working for James Dole (of Dole Pineapple) invented a machine to slice pineapples into rings.

In 1925, the Hawaiian Pineapple Company sponsored a contest for pineapple recipes with judges from the Fannie Farmer’s School, Good Housekeeping, and McCall’s Magazine. More than 2,500 of the 60,000 submissions were recipes for pineapple upsidedown cake. The company decided ran an ad about all of these pineapple upside-down cake recipes, and that made the cake even more popular.

The Maraschino cherry was introduced into America in the late 19th century and was used in cocktails as well as to decorate many food items, including hams, milkshakes, sundaes. It adds a bright finishing touch to the pineapple upside down cake.


1 1/2 sticks butter
2 cups light brown sugar, packed
1 large can pineapple slices, drained (reserve the juice)
maraschino cherries
3 eggs
1 tsp. vanilla extract
1 cup white granulated sugar
1 1/2 cups plain flour
2 tsp. baking powder
1/4 tsp. salt


Preheat oven to 350 degrees.

  1. Use a 10 inch round iron skillet. Melt the butter over low heat. After melted remove from heat and mix in the brown sugar.
  2. Place 8 slices of pineapple in bottom of skillet, then pour in butter and brown sugar mixture, Place a maraschino cherry in middle hole of each pineapple in the skillet.
  3. In a large bowl, separate the eggs and reserve the egg whites. Place the yolks in another bowl. Beat the egg yolks until lightly fluffy, Set aside.
  4. Combine 1/2 cup of pineapple juice, the white sugar, and vanilla. Mix until the sugar is dissolved.
  5. Slowly add this mixture to egg yolks, mixing well.
  6. Sift the baking powder, flour, and salt into the egg mixture. Combine well.
  7. Beat the egg whites until stiff and then fold them into yolk mixture.
  8. Add this mixture to the butter, pineapple, and sugar mixture in the skillet.
  9. Bake at 350 degrees for 35 minutes. Let it cool for 10 minutes. Then turn up side down cake onto a plate.

It is one of those great retro cake recipes!

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