Last updated on March 8th, 2022
Here’s the printable recipe from my “Skillet Pineapple Upside Down Cake” video that was recently published on YouTube. This 1920s dessert is moist and buttery with a caramelized brown sugar and pineapple topping. It’s beyond easy to make. All you need is an oven-proof skillet!
Watch the video above to see how quickly Pineapple Upside Down Cake comes together. Then scroll down for historical notes and the printable recipe. Hungry for more? Get my email updates.
Upside-down cakes have been around for hundreds of years (see my recipe for Tarte Tatin). Pineapple upside down cakes became popular in the mid-1920s, after the Hawaiian Pineapple Company (now Dole Company) sponsored a contest for pineapple recipes. From the 60,000 submissions they received, approximately 2,500 were for Pineapple Upside Down Cake! The company ran ads for the inverted cake, which increased the cake’s popularity.
My Thoughts on Maraschino Cherries
You have probably seen Pineapple Upside Down Cakes decorated with eye-poppingly-red maraschino cherries. I omit these cherries for three reasons: 1) Their brilliant hue is completely unnatural — it comes from food coloring; 2) a yellow-and-red color scheme is offensive to me (I’d never put red pillows on a yellow sofa), and 3) the cake doesn’t require extra adornment! Of course, I am not the boss of you. If you like maraschino cherries, then by all means add them.
Alright then. Here’s the printable:
Skillet Pineapple Upside Down Cake
For the pineapple topping:
- 1/2 cup (113g) butter
- 1/2 cup (100g) brown sugar (light or dark as you please)
- 20 ounce can pineapple slices, drained
For the cake:
- 1/2 cup (113g) butter, softened to room temperature
- 3/4 cup (150g) white granulated sugar
- 2 large eggs, at room temperature
- 1 teaspoon pure vanilla extract
- 1 1/2 cups (190g) self-rising flour* (sift first if not measuring by weight)
- 1/2 cup whole milk
Preparing the pineapple topping:
- Center the oven rack, and preheat the oven to 350°F. In a well-seasoned 10-inch-diameter cast-iron skillet, melt the 1/2 cup butter over medium heat. Off heat, immediately sprinkle the brown sugar over the melted butter. Arrange 7 pineapple slices in the skillet. Set aside.
Making the cake batter:
- Put the 1/2 cup softened butter, the white sugar, and the eggs in a large mixing bowl. Use electric hand-held beaters to cream the mixture until it is light and fluffy -- about 3 minutes. Use a spatula to stir in 1/3 of the self-rising flour. Then stir in half of the milk. Repeat with another 1/3 of the flour and the remaining milk. Then stir in the remaining flour. Briefly beat with the electric beaters until all ingredients are thoroughly combined -- not more than 30 seconds.
Assembling and baking the cake:
- Spoon the batter over the pineapples in the skillet, and gently smooth the top with the back of the spoon. (Don't worry if some of the melted butter creeps up over the batter.) Bake in the preheated oven until the cake puffs and lightly browns -- usually 30 minutes.
Unmolding the cake:
- While the cake is still hot, run a knife between the edge of the cake and the wall of the skillet. Place a large plate or platter on top of the skillet. Then, being sure to protect your hand from the hot handle, invert to unmold.
- Although the cake is wonderful at any temperature, it is particularly delicious when served warm. Enjoy it with champagne for dessert, or with coffee for breakfast!