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Tipsy Pineapple Upside Down Cake


Pineapple Upside Down cake is a classic retro cake. It is said that it was originally created back in 1925, when Dole first developed a way to core and slice pineapples as a canned item. I make my cake in a cast iron skillet, and I'm 100% loyal to using maraschino cherries, instead of pecans. (I figure a little Red-Dye 40 is no biggie, since I don't make this cake all the time.)I love how the cake is flipped onto a plate, once it's done, and all the butter and brown sugar has caramelized the pineapple. Don't let the recipe name scare you-- you won't get tipsy from the rum in this recipe. I have never added rum to my pineapple upside cakes, until now. I'm so glad that I did! You can't taste the rum, but it certainly added extra flavor to the pineapple and cake. Trust me. It's best enjoyed, served slightly warm. A dollop of freshly whipped cream is a nice touch, too.
This recipe is slightly adapted from:

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  • For the topping:
  • 1/2 cup butter (I suggest using 3/4 stick butter)
  • 1 cup brown sugar (my suggestion is to use 3/4 cup brown sugar
  • 1 Tbsp dark rum (optional, but worth it)
  • Approximately 9 slices of cored pineapple (20 oz of sliced pineapple, fresh or canned
  • 9-10 Maraschino cherries (optional, but my favorite choice. Can replace with pecans, if preferred.
  • For the Cake:
  • 1 cup flour
  • 1 tsp baking powder
  • 1/8 teaspoon salt
  • 3 eggs, separated
  • 1 cup sugar
  • 5 Tbsp dark rum (or substitute with pineapple juice--I used 3 Tbsp dark 1 teaspoon pure vanilla extract


Adapted from


Step 1

Preheat oven to 350 degrees; position a rack in the center of the oven.
NOTE: I prefer a to use my cast-iron skillet, but you can use a 9" cake pan as well.

If using a cast iron skillet, melt the butter on low heat. Otherwise,
add the butter to a 9-inch-round baking pan. Place the pan inside of the pre-heated oven until melted, about 5 minutes.

Once the butter has melted in the skillet, add the brown sugar and rum; stir until mixed well and even. Otherwise, remove the pan from the oven and then add the brown sugar and rum.

Arrange the pineapple slices evenly in the pan; place a cherry in the center of each one and fill the center and any other open space with either additional pineapple pieces or pecans.
NOTE: I recommend decreasing the butter and brown sugar by 25%, as I found the cake to be on the borderline of "almost too sweet".

To make the cake:
In a medium bowl, combine flour, baking powder and salt and whisk to combine.
Using a stand mixer, beat the egg whites until fluffy; scrape into a clean bowl.
Using the same mixing bowl, beat the egg yolks and sugar until thick and creamy; add the rum and vanilla extract and mix well.
Add the flour mixture and beat until well combined.
Using a spatula, fold in the egg whites until just mixed in.
Pour the batter over the fruit in the cake pan and smooth to the edges.
Bake for 30 minutes until the cake is golden brown and a toothpick inserted into the center comes out clean.
NOTE: Suggested time was 40 minutes, but my cake was ready in 30 minutes.
Place on a wire rack to cool for 10 minutes.
Run a knife around the edges of the pan to loosen the cake. Place a serving plate over the pan and invert carefully allowing the cake to slide out of the pan.
Serve warm or at room temperature; dollop with whipping cream if desired.


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