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Pineapple Upside Down Cake

Probably no vintage dessert speaks to a bygone era more than the pineapple upside cake. Growing up in South Texas, the sweet, moist dessert was popular at Sunday dinner, school cakewalks, church potlucks, and funeral meals. Although the cake has been around for hundreds of years, it wasn’t until the early 1900s that its popular form came to be. That was when James Dole, founder of the Hawaiian Pineapple Company, now known as Dole, created the perfect way to can the sweet fruit.

Prior to Dole’s innovation, much cooking in the region was done in cast iron skillets over an open flame. When they wanted something sweet, fresh fruits would be cooked with sugar, and a batter poured on top. Once done, as today, the dish was flipped over, presenting the pretty, caramelized bottom of the dessert.

Today, the cake is usually prepared using canned pineapple rings, dotted with maraschino cherries. In addition to making an artful presentation, the fruit rings allow the cake to be sliced neatly in even portions. I decided to prepare the cake in a semi-version of the original, using fresh pineapple. The result was delicious.

A brilliant thing about this cake is that it can be made with a quality yellow cake mix and still taste as good. If using a mix and canned fruit, use the fruit’s juice in place of water (using additional water if the can’s juice doesn’t equal the mix directions). This adds a kick to the flavor and heightens moisture. For a more tropical feel, I often add a cup of chopped roasted macadamia nuts to the topping before baking.

Cake Ingredients

3 cups all-purpose flour

2 cups sugar

1 Tbsp. baking powder

1 ½ cups milk

1/2 cup butter, softened

½ Tsp. vanilla

2 eggs

Topping Ingredients

1/3 cup butter

2/3 cup light brown sugar

Pineapple from one medium-sized fresh, ripe pineapple, peeled, cored, and chopped

Maraschino cherries, chopped


  1. Preheat oven at 375˚. Coat a 9 x 13-inch baking pan with cooking spray and set aside.

  2. In a large mixing bowl, combine flour, sugar, and baking powder. Add milk, butter, and vanilla. Beat on low speed until combined. Increase the mixer speed and beat on high for 2 minutes. Add eggs and beat 2 minutes more. To keep cake light, don’t over process. Set batter aside.

  3. In a small saucepan, melt butter and brown sugar over medium heat, stirring often. Heat until the mixture is bubbly, and sugar dissolved. Pour butter/sugar mixture into the baking pan. While still hot, layer pineapple evenly over the mixture and add cherries (Don’t worry if caramel mixture appears to be hardening). Refrigerate any leftover pineapple to enjoy later.

  4. Pour cake batter evenly over pineapple mixture and bake for 30 to 35 minutes or until a toothpick inserted near the center comes out clean. Because oven temperatures can vary, keep an eye on the cake once it reaches the 30-minute mark, adjusting baking time.

  5. Cool on a wire rack for five minutes. Loosen sides with a table knife and invert onto a platter. Allow to cool before slicing.


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