I don’t know how this started, but when I was a little kid and well into my teens, my birthday was accompanied by two pineapple upside down cakes. The first was for my guests: friends, family, and anybody else who happened to swing by. The second was entirely for me. If I’m ever home for my birthday, my mom will still do this for me.
It may sound preposterous, but a pineapple upside down cake never lasts more than 24 hours in my house. I eat a piece or two for breakfast, a piece for lunch, a follow up for dinner, and something before bed because why would you ever leave one piece of cake for the next day?
This recipe changes the traditional butter-sugar syrup for a butter smear made from rich ingredients that completely transforms in the oven to form a crisp caramel like coating. You can also see by the photo above that I’m a bit ridiculous and have a pan that is designed for pineapple upside down cake. Don’t judge. I bet you have some ridiculous things in your house too. I love this pan because I can make individual cakes, freeze some, and take them out whenever I feel like a treat. If you are not so inclined to own this pan, I’ve included instructions on how to make this cake in a 9 inch cake pan in the variation section at the bottom.
Ingredients (makes 6 cakes)
- 2 sticks unsalted butter, room temperature
- 8 pineapple slices
- 8 maraschino cherries
- 1 1/3 c all purpose flour
- 1 c brown sugar
- 1/2 c + 2 tbsp granulated sugar
- 3 tbsp milk
- 2 tbsp baking powder
- 1 1/2 tbsp honey
- 1 tsp rum
- 3/4 tsp vanilla extract
- 2 eggs
1. Preheat the oven to 350 degrees. Place 1 stick of butter, brown sugar, honey, rum, and 1/4 tsp vanilla in a bowl. Blend until well combined. Smear 1/3 of the mixture into the cake pan.
Note: This recipe makes enough smear for 3 cakes. It will keep in the refrigerator for two weeks, or you can portion it into plastic wrap and freeze until you are ready to use.
2. Place 1 pineapple slice into each slot (arrange 8 slices if using a 9 inch cake pan) and
place a cherry in the center of the pineapple. Set aside while you make the cake batter.
3. Place the other stick of butter and granulated sugar in a mixer with a paddle attachment. Turn to low and combine the ingredients. Then turn the mixture up to medium and cream the ingredients for 3 minutes.
4. Add the eggs, milk, and 1/2 tsp vanilla extract. Mix to combine. Slowly add the flour to the mixture 1/3 c at a time. Add the baking powder and mix to combine all ingredients. The batter will be pretty thick. Distribute the batter into the cake pans and make your best attempt to level it out. While cooking, the butter in the batter will melt and the cake will even out, so just make you best effort.
5. Cook for 15 minutes. Rotate the pan to ensure proper browning. Cook for another 10 minutes or until a toothpick inserted into the center comes out clean.
6. Let the cakes cool in the pan for 5 minutes. Turn the cakes onto a cooling rack and let cool. Enjoy.
Nine Inch Cake Pan Instructions
Make the smear and spread 1/3 of the mixture on the bottom of the pan. Arrange the pineapple slices around the edge of the pan and place one slice in the middle. Prepare the cake batter as is.
Cook for 20 minutes and rotate. Then cook for another 20 minutes or until a toothpick placed in the center comes out clean.