Pineapple Upside-Down Cake

This cake is the perfect dessert to make in a cast-iron skillet. Making the caramel in the pan and then pouring the cake batter on top makes the caramel become part of the cake.


1 18-ounce can pineapple rings

4 tablespoons butter

½ cup brown sugar

7 maraschino cherries

4 tablespoons cold butter

1 cup brown sugar

2 large eggs

½ cup milk

½ cup sour cream

1½ teaspoons vanilla extract

1½ cups all-purpose flour

1½ teaspoons baking powder

½ teaspoon salt

  • Preheat oven to 350°F. Place a skillet over medium-high heat. Drain the juice from the can of pineapple into the skillet. Add 4 tablespoons butter and ½ cup of brown sugar. Stir with a wooden spoon as everything melts. Boil to a thick caramel-like consistency. Turn off the heat, lay 6 pineapple rings around the outside and 1 in the center of the skillet with a maraschino cherry in the center of each ring. Place in the oven to preheat the pan while you prepare the cake.

  • Combine the cold butter and sugar in a mixing bowl until it is light and creamy. Beat in the eggs one at a time. Make sure the first egg is completely incorporated before mixing in the second. Add the milk, sour cream, and vanilla. Stop mixing once it is combined but not smooth.

  • Sift together the flour, baking powder, and salt. Use a spatula or spoon to fold in the wet ingredients. Remove the skillet from the oven and pour the batter in. Gently shake the skillet back and forth to even out the batter. Bake for 45–50 minutes.

  • Let sit for 5–10 minutes. Place a large plate upside down on top of the skillet. Turn the skillet upside down. If any caramel or fruit sticks, remove with a spatula and place it back on the cake. Let the cake cool for 10 minutes before serving.

The Flip Side of the Pineapple Upside-Down Cake

In 1925, the Hawaiian Pineapple Company ran ads looking for creative pineapple recipes. They received 1,500 recipes for the pineapple upside-down cake. The winning entry came from Mrs. Robert Davis of Norfolk, Virginia, and was published in their cookbook.

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