You can't go wrong with a classic dessert like a pineapple upside-down cake. The sugary, buttery topping adorned with the vintage pineapple slices and maraschino cherries makes for not only a beautiful presentation, but a wonderful and delicious cake.
There are a variety of ways you can make this cake; each method produces a scrumptious dessert.
Whether you want to make the cake in a cast-iron skillet or bake it in the oven in a cake pan, you'll end up with a beautiful upside-down cake. I decided to use the cake pan technique because that's the method my mom and I use every time we make a pineapple upside-down cake.
The first step with every upside-down cake is to make the topping. It sounds weird, but because you flip the cake after it bakes, you have to put the gooey topping on the bottom of the pan first.
Heat four tablespoons of unsalted butter with 3/4 cup of light brown sugar in a sauce pot until the butter completely melts and the sugar crystals dissolve. Keep the pot on the heat and stir the mixture until it starts to caramelize. You will know that the sugar and butter have started to caramelize when bubbles appear on the edges of the mixture; it will be thick and viscous as well.
Pour the butter and sugar into a greased nine-inch cake pan that has three-inch sides. Spread the topping evenly over the bottom of the cake pan.
Next, place pineapple slices around the cake pan in a circle, ending with one in the middle. You can use pineapple slices from a can (I did), or you can cut your own pineapple slices. I always use the canned pineapple slices because they are all the same size, which helps create a nice presentation. Finish the topping with a maraschino cherry in the middle of each pineapple slice.
Now it's time to make the cake. Sift 1 1/2 cups of all-purpose flour with two teaspoons of baking powder and 1/4 teaspoon of salt. Then, beat 1/2 cup of unsalted softened butter with one cup of sugar. Once the mixture is creamed, add one teaspoon of vanilla extract. Then, add two egg yolks, one at a time. Alternately add the flour mixture and 1/2 cup of milk, starting and ending with the flour.
In another bowl, combine the two egg whites with 1/4 teaspoon of cream of tartar and whisk until firm peaks are formed.
Finish the cake batter by folding in the egg whites. This will make the cake light and fluffy.
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Pour the cake batter into the cake pan over the pineapple and cherry topping, then bake for 45 minutes in a preheated 350 degree oven. You'll see that the top of the cake will be slightly golden once it is done.
Remove the cake from the oven and let it cool for approximately ten minutes. Once it is cooled, gently run a knife around the edges of the cake to separate it from the sides of the pan. Place a plate on top of the cake and flip the cake to reveal the gooey, sticky pineapple topping.