UpSide Down Cake

A special dessert treat when we were growing kids was pineapple upside down cake. Rich, caramel flavored sauce, sweet pineapple and bright red Marischino cherries and soft and sweet cake, what’s not to like? I can remember that it was always made in a cast iron skillet. That would be a holdover from my dad’s childhood when cakes were skillet cakes and cooked on the top of the wood-burning stove. Back then in the woods of Upper Peninsula Michigan it was apple and cherry skillet cakes.

After the discovery of pineapple by the first European explorers of the new world, the fruit became a world trade good. But as a fresh fruit, distribution was coastal and expensive. In 1903 Dole began canning pineapple in Hawaii and pineapple was available to all. By the 1920's, canned pineapple was a staple item in most food stores. That would be about the time that my dad and aunts moved to wild and wicked Hollywood. There they would become acquainted with pineapple and the a newly popular recipe, pineapple upside down cake. They would use the same cooking methods they learned at grandmother's side over the wood-burning stove.

In immitation, I use a 10-inch cast iron skillet to make the cake. It is a perfect-sized pan. You can use regular cake pans but you have to very careful not to scorch the butter and brown sugar.

Preparation: 45 minutes Heirloom Recipe
Serves 8 to 10 persons Margie Alena Gilliland
  • Fruit and Frosting Glaze
  • 3/4 cup butter or margarine
  • 1 20-ounce can pineapple slices
  • 7 to 19 Maraschino cherries, as desired
  • 3/4 cup dark brown sugar
  • 1/4 cup pineapple packing juice
  • Cake
  • 2/3 cup granulated sugar
  • 2 tablespoons butter
  • 1 cup cake flour
  • ½ teaspoon salt
  • 1 teaspoon baking powder
  • 2 whole eggs
  • ½ teaspoon vanilla extract
  • 1/4 cup whole milk
  1. Drain pineapple reserving 1/4 cup of the packing juice. Keep 7 rings intact, cut 3 rings in half. Set aside.
  2. Over medium heat, melt butter in cast iron frying pan. Add brown sugar while stirring, until dissolved. Add pineapple juice and cook and stir until mixture is bubbling. Remove from heat.
  3. Arrange the seven pineapple rings in the bottom of the pan in the hot glaze. Use the end of the spoon to gently press the rings down. Arrange the half rings around the edge of the frying pan. Place a Maraschino cherry in the center of each pineapple ring and in the spaces betweent he rings as desired.
  4. You can use a packaged yellow or white cake mix with good results - use package directions.
  5. Or, make cake as follows: Mix flour, salt and baking powder togther and set aside. Cream together sugar and butter. Add eggs. Milk and vanilla and beat until smooth and creamy. Slowly add dry ingredients and mix just until well blended, about 1minute.
  6. Carefully pour the batter over the top of the pineapple rings. Bake in a preheated 350°oven for 30 minutes or until golden brown and a toothpick inserted into the middle of the cake comes out clean.
  7. Allow to cool for 30 minutes. Carefully run a kitchen knife or spatula around edge and along side of frying pan to loosen cake. Invert platter over the top of the pan and turn upside down. Remove pan. You can serve right away but it slices easier when allow to finish cooling.
  8. A picture-pretty cake that will please your family and guests but it is so easy and quick to make.

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Latest revision done January 2007
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