Pineapple Upside Down Cake is a recipe that dates back to the 1920s when the Dole Company had a cooking contest using canned pineapple. The Hawaiian Pineapple Company was founded in 1901 by James Dole and would eventually become the Dole Food Company.
Jim Dole developed a way to slice and can pineapple in 1903 and in 1925 ran a contest using the fruit resulting in over 2,500 entries which was considered phenomenal for the time. The original recipe for Pineapple Upside Cake was made in an iron skillet.
Skillet cakes were common in the days of ovens fired using wood and coal. Since maintaining an even temperature was hard, using a skillet allowed one to move it on and off the heat to cook more evenly.
Newer recipes for Pineapple Upside Down Cakes range from those gourmet recipes that call for using fresh pineapple and making homemade caramel to the other extreme where you use a yellow cake mix. However, the original recipe that was included in The Fannie Farmer Baking Book, is easy to make, the presentation is lovely, and it tastes great, too. Sometimes the original needs no improvement!
If you’ve never had Pineapple Upside Down Cake or if you haven’t had it in a long time, you might want to try it soon. The cake is not overly sweet and pairs well with the sweet sugar and pineapple. Served warm with a side of freshly whipped cream – there’s almost nothing better than this old fashioned, comfort food dessert.
Oh, and if you don’t have an iron skillet, do not despair. You can make this cake in a 9-inch round cake tin, too.
Pineapple Upside Down Cake ingredients.
Drain seven pineapple slices and seven maraschino cherries.
Place the flour, baking powder, and salt into a bowl and whisk or sift until well combined. Set aside.
Cream the shortening in a large mixing bowl gradually adding the sugar and beating well. Scrape down the sides of the bowl if necessary.
Add the eggs, one at a time, and beat well. Add the vanilla and beat until the mixture is well blended and fluffy. Scrape down the sides of the bowl if necessary.
Add the dry ingredients and milk and beat until the mixture is perfectly smooth. This will take about 30 seconds. Do not overmix.
The batter should be perfectly smooth. Set aside.
Melt the butter in the 9-inch cast iron skillet over medium heat until melted. Add the brown sugar and, stir constantly, until the sugar is dissolved and the mixture is bubbly. Remove from heat.
Place seven pineapple rings directly onto the sugar mixture. Place a cherry into the center of each pineapple ring.
Spread the batter over the pineapple layer.
Bake in a preheated oven for 35 to 40 minutes or until a toothpick inserted into the center comes out clean.
Allow to cool for 5 minutes before turning out onto a cake plate.
 
Serve warm with whipped cream.
Yummy.
Pineapple Upside Down Cake Adapted from The Fannie Farmer Baking Book, Copyright © 1984 Makes one 9-inch round cake, serves 6 to 8 1 2/3 cups all-purpose flour Preheat oven to 350°F. Combine the flour, baking powder, and salt in a bowl and whisk or sift to combine well. Set aside. In a large mixing bowl, cream the shortening. Add the sugar, gradually, and beat well. Add the eggs, one at a time, beating well after each addition. Add the vanilla and continue to beat until the mixture is well blended and fluffy. Add the dry mixture and milk to the shortening mixture and beat until the batter is thoroughly combined and perfectly smooth. This will take about 30 seconds. Do not overmix. Set aside. If using a 9-inch skillet, place it on the stove over medium heat and add the butter. Once the butter is melted, add the brown sugar and cook, stirring constantly, until the sugar melts and is very thick and bubbly. If using a 9-inch cake pan, prepare the butter and brown sugar mixture in a saucepan. Then pour it into the cake pan. Rapidly, arrange the pineapple slices in one layer in the skillet or cake pan, pressing them down into the hot syrup. Place a cherry in the center of each ring. Spread the batter evenly over the pineapple rings. Bake for 35 to 40 minutes or until a toothpick inserted into the center of the cake comes out clean. Remove from the oven and let cool in the pan for about 5 minutes. Turn out onto a serving plate. Serve warm with whipped cream.
2 tsp baking powder
¼ tsp salt
1/3 cup vegetable shortening
2/3 cup sugar
1 tsp vanilla
2 eggs
2/3 whole milk
4 TB butter
¾ cup dark brown sugar
7 pineapple rings (one 8-ounce can of pineapple slices contains 4 rings and one 20-ounce can of pineapple slices contains 10 rings)
7 maraschino cherries
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