Bourbon-Soaked Pineapple Upside-Down Cake
Want to know a secret? There was an episode of MasterChef where we only had a cast iron skillet, a paring knife, a wooden spoon, and a cutting board to compete. I ended up making a beautiful chicken thigh dish that got rave reviews, but that wasn't the first dish that came to mind for me. The first thing I thought of was pineapple upside-down cake, perfect in a cast iron skillet, but I changed my mind after realizing I'd have to break down a pineapple with a paring knife.
You can use canned pineapple slices for this cake, but soaking fresh pineapple in bourbon enhances this classic cake in the most delicious way. I prefer fresh pineapple when including bourbon because it has a chance to take on more flavor. Canned pineapple has already sat in juice for a long time, so it will not take on as much of the brown sugar and bourbon. It's also nice to have leftover pineapple in bourbon soak for cocktails!
A good cocktail is also why I choose to use amarena cherries instead of maraschino. I learned about these cherries on a visit to Jeni's Ice Cream years ago, and I couldn't believe what I was tasting and how it melted in my mouth like candy. Fast forward to my passion for all things bourbon, and I learned that these cherries are used in cocktails far more than maraschino cherries are. I've even purchased amarena cherries that are soaked in bourbon! Amarena cherries are dark, wild cherries packed in a delicious syrup that takes on the color of the cherries. They originated in Italy and made their way to the United States to enhance decadent chocolate desserts. I find these at Trader Joe's, but you can also order these online.
When assembling bourbon-soaked pineapple upside-down cake, it's important to remember that less is more. Less moisture means a gooey, better set topping. Pineapple retains a lot of water; this pineapple has been soaking in bourbon. That is why I lightly blot each pineapple ring with a paper towel. The goal is not to remove all the flavorful bourbon soak. We're simply trying to remove any dipping liquid that will make the brown sugar dissolve. Less liquid means more success with inverting a cake with a topping that sticks!
This cake recipe is a pretty standard white cake recipe, and I prefer more egg white than egg to help keep the cake light and fluffy. No matter how often I try to convince myself that all-purpose flour will work for a white cake, I'm always wrong—every single time. Lighter, finer cake flour is the only way to go when making a white cake, and it has always given me the results I prefer. Make sure you are giving the soft butter proper time to get light and fluffy. It will become fluffier by continuing to scrape the sides of the bowl when you add sugar. All that beautiful air whipped into that butter helps it stay light and fluffy.
This upgraded classic cake is the cake of my MasterChef dreams, although it's much dreamier now that I can make it without being timed! I hope you enjoy it as much as I do.
Bourbon Soaked Pineapple Upside Down Cake
Ingredients
- 1 fresh pineapple, cored and sliced
- ½ cup bourbon
- 2 tbsp brown sugar
- ¼ cup butter, melted
- ½ cup dark brown sugar
- 5-6 Bourbon Soaked pineapple rings
- 20-25 amarena cherries
- 2 tbsp amarena cherry liquid
- 2 cups cake flour
- 1 tsp baking powder
- ¼ tsp baking soda
- ½ tsp salt
- 8 tbsp butter, softened
- 1 cup sugar
- 2 eggs whites
- 1 whole egg
- ½ cup sour cream
- 1 tsp vanilla extract
- 2 tbsp reserved bourbon pineapple liquid
- 3 tbsp whole milk
Instructions
- Begin by mixing 2 tbsp brown sugar with ½ cup bourbon in an airtight container. Add the pineapple and allow it to marinate in the sweet bourbon mixture refrigerated overnight.
- Preheat the oven to 350 degrees.
- Prepare the topping by pouring ¼ cup melted butter into a 10” cast iron skillet or a deep round cake pan. Sprinkle the brown sugar over the melted butter evenly, being sure to cover the entire bottom of the pan. Remove 5-6 pineapple rings from the sweet bourbon mixture. Set the reserved sweet bourbon mixture aside. Gently blot pineapple with a paper towel. Lay the pineapple rings on top of the brown sugar, covering as much of the brown sugar as possible. Follow behind with the amarena cherries, making sure to remove any stems. Drizzle 2 tbsp cherry liquid over the patterned pineapple and cherries. Place the skillet in the refrigerator for at least 30 minutes.
- While the fruit is chilling, prepare the cake batter by whisking the cake flour, baking powder, baking soda, and salt. Set aside.
- Using a stand mixer with the paddle attachment, beat the butter on high speed until creamy. Add the sugar and continue beating until well combined. Scrape the sides of the bowl before beating in egg whites one at a time. Continue beating and add whole eggs. Scrap the sides of the bowl. Return mixer to medium-high speed and beat in sour cream. Mix in vanilla extract and 2 tablespoons of reserved sweet bourbon mixture.
- Reduce the mixer speed to low and alternate between 1/3 of the flour mixture with 1/3 milk into the bowl one at a time. Be sure to mix on low until fully combined before adding the next ingredient. Start and end with flour. Do not overmix. Turn off the mixer as soon as all ingredients are fully combined.
- Pour cake batter over the chilled fruit topping and spread evenly to ensure no topping is exposed and cake batter is even. Bake for 40-45 minutes. The cake is done when a toothpick inserted into the center of the cake comes out clean.
- Carefully remove the cake from the oven and allow it to cool on a cooling rack for 20-30 minutes. Invert the warm cake onto a cake stand or plate. Allow the cake to continue cooling before slicing.
- Cover remaining cake slices with plastic wrap and refrigerate for up to 5 days.
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