Nothing screams retro dessert quite like a Pineapple Upside-Down Cake. The sweet, caramelized pineapple rings and cherries sitting on top of a moist, buttery cake is an old-school favorite that never goes out of style. Plus, it’s as visually stunning as it is delicious. And the best part? You can make it all in one skillet!

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Why You’ll Love This Recipe

Classic and Timeless: This dessert has been a favorite for decades and brings nostalgia with every bite.
Caramelized Topping: The buttery brown sugar topping paired with juicy pineapple and cherries is simply irresistible.
One-Skillet Wonder: Made in a cast iron skillet, the cake bakes to perfection, and flipping it out reveals a stunning presentation.

Ingredients for Pineapple Upside-Down Cake

1/2 cup melted butter: This adds rich flavor and helps create that gooey caramelized topping.
1 cup brown sugar: Forms a sweet and sticky layer with the melted butter, creating that signature caramelization.
1 small can sliced pineapple: The star of the show! Pineapple rings give the cake its iconic look and flavor.
7-10 maraschino cherries: Bright, red cherries add a fun pop of color and sweetness.
3 eggs, beaten: The eggs provide structure and richness to the cake batter.
1 cup granulated sugar: Sweetens the cake and balances the tartness of the pineapple.
1 cup sifted all-purpose flour: The base for a soft and fluffy cake.
1 tsp baking powder: Helps the cake rise to the perfect texture.
1/4 tsp salt: Enhances the flavors and balances the sweetness.
5 tbsp pineapple juice: Adds a fruity kick and keeps the cake moist.

How to Make Pineapple Upside-Down Cake

Step 1: Prepare the Skillet

Start by preheating your oven to 350°F (175°C). Grab a heavy cast iron skillet, melt 1/2 cup of butter over medium heat, and stir in 1 cup of brown sugar until the sugar dissolves and blends into the butter, creating a rich caramel sauce. Once blended, remove from heat.

Step 2: Arrange the Pineapple and Cherries

Arrange the pineapple slices in the bottom of the skillet, placing one ring in the center and fanning the rest around the edges. In the center of each pineapple slice, pop a maraschino cherry for a colorful and classic look.

Step 3: Make the Cake Batter

In a large bowl, mix together 3 beaten eggs, 1 cup of sugar, 1 cup sifted all-purpose flour, 1 teaspoon baking powder, 1/4 teaspoon salt, and 5 tablespoons pineapple juice (from the can of pineapples). Stir until just combined and smooth.

Step 4: Pour and Bake

Carefully pour the cake batter over the pineapple slices in the skillet, spreading it out evenly so it covers all the fruit. Place the skillet in your preheated oven and bake for 35 to 40 minutes, or until the top is golden brown and a toothpick inserted into the center comes out clean.

Step 5: Cool and Flip

Once the cake is baked, let it cool in the skillet for about 5-10 minutes. Then, run a knife around the edges of the cake to loosen it. Place a large serving plate over the skillet, and with confidence, flip the skillet upside down so the cake lands on the plate, revealing the beautiful pineapple and cherry topping.

Pro Tips for Success

Don’t Overmix the Batter: When combining the dry and wet ingredients, mix just until combined. Overmixing can lead to a denser cake.
Cool Slightly Before Flipping: Let the cake cool for a few minutes before flipping to ensure the caramelized topping sets but doesn’t stick to the skillet.
Serve with Ice Cream: For an extra indulgent treat, serve this cake warm with a scoop of vanilla ice cream, just like your hubby likes it! The warm cake and cold ice cream are a dreamy combination.

Variations to Try

Spiced Pineapple Cake: Add a teaspoon of cinnamon or a dash of nutmeg to the cake batter for a cozy twist.
Coconut Pineapple Upside-Down Cake: Sprinkle shredded coconut over the brown sugar before adding the pineapple for a tropical vibe.
Raspberry Substitute: Instead of cherries, try placing raspberries in the center of the pineapple slices for a fresh burst of flavor.

Storing and Reheating

Storing: Leftover cake can be stored in an airtight container at room temperature for up to 2 days or in the fridge for 3-4 days.
Reheating: To reheat, warm slices in the microwave for 10-15 seconds to enjoy that melty, caramelized topping again.

Final Thoughts

This Pineapple Upside-Down Cake is an easy-to-make yet impressive dessert that will have everyone reaching for seconds. Whether served at a family gathering, holiday dinner, or a casual weeknight treat, this cake brings a sweet slice of nostalgia with every bite. And don’t forget the ice cream on top!