I Made the 1926 Recipe for Dole Pineapple Upside-Down Cake—and I’m Head Over Heels

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This is the contest-winning recipe that kicked off America's obsession with pineapple upside-down cake. It's as good today as it was in 1926!

I love a good retro recipe—and this one has been around for nearly 100 years. The pineapple upside-down cake saw a mid-century peak in popularity but continues to be a favorite potluck dessert. The best thing about this cake is its dramatic reveal: flipped upside down after baking, the perfectly placed pineapple rings and cherries emerge, coated in a buttery brown sugar syrup that soaks into the sweet cake. Lovely!

There are many pineapple upside-down cake recipes out there today, including variations like rum-soaked cakes and Duncan Hines’ two-tier, frosted version. But I decided it was time to go all the way back to 1926 to test the recipe that kicked off the pineapple upside-down cake craze: Dole’s pineapple upside-down cake.

Who Invented Pineapple Upside-Down Cake?

For starters, upside-down cakes made with fruit like apples, plums and cherries were popular through the late 19th century. The fruit and sugar caramelized on the bottom of the pan while the cake batter baked above.

By the 1920s, canned pineapple was widely available in the States, and in 1925, Dole held a pineapple recipe contest. The winner was a pineapple upside-down cake recipe submitted by Mrs. Robert Davis from Norfolk, Virginia. However, a whopping 2,500 people sent in recipes for the same cake, so it’s unclear who the true inventor was.

Dole decided to promote the tasty recipe in magazine ads and articles, and it became an extremely popular dessert, especially through the ’50s and ’60s.

How to Make Pineapple Upside-Down Cake

This is the original recipe that won the 1926 Dole Pineapple Company contest. I made one change: to add the maraschino cherries to the pan with the pineapple, instead of garnishing the cake with cherries after baking. The cake bakes up beautifully in a cast-iron skillet, but you can also use a 9-inch round cake pan. It makes 6 to 8 servings.

Dole Pineapple Upside Down Cake ingredientsNancy Mock for Taste of Home

Ingredients

  • 2 cups all-purpose flour
  • 2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/2 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 2 large eggs, whites and yolks separated
  • 1/2 cup milk
  • 1 teaspoon vanilla extract

Assembly:

  • 2 tablespoons unsalted butter
  • 1 cup packed brown sugar
  • 1 large (20-ounce) can pineapple rings
  • 10 maraschino cherries, stems removed

Editor’s Tip: Use one of our easy methods to separate egg whites from yolks.

Tools You’ll Need

  • Cast-iron skillet: Use your handy cast-iron skillet (or another oven-proof skillet) to bake this upside-down cake.
  • Stand mixer: This Kitchen-Aid stand mixer is top-ranked by our Test Kitchen staff.
  • Round cake platter: You’ll need a large platter with a lip that will hold in the puddle of sugary syrup that flows from this cake!

Directions

Step 1: Prepare the cake batter

Dole Pineapple Upside Down Cake prep cake batterNancy Mock for Taste of Home

Preheat the oven to 350ºF. Sift together the flour, baking powder and salt—then hold this aside. Cream together the softened butter and sugar in the bowl of a stand mixer, until the mixture is light in color. Add in the egg yolks, and mix until they’re blended in.

Add the flour mixture in batches alternating with the milk, running the mixer at low speed until the ingredients are just combined. Stir in the vanilla extract.

Step 2: Fold in the egg whites

Dole Pineapple Upside Down Cake fold in egg whitesNancy Mock for Taste of Home

Use a hand mixer to beat the egg whites in a small bowl, until they’re fluffy with stiff peaks. Stir in a third of the egg whites by hand to help loosen the batter.

Then fold the remaining egg whites into the batter by gently scooping the batter up and over the whites—this will help keep the airy texture in the egg whites. Fold until the egg whites are incorporated into the batter.

Step 3: Prepare the skillet with butter and brown sugar

Dole Pineapple Upside Down Cake brown sugar skilletNancy Mock for Taste of Home

Melt the 2 tablespoons of butter in a cast-iron or another oven-proof skillet over medium heat. Tilt the pan around so that the melted butter coats the bottom and sides of the pan. Remove the pan from heat, then sprinkle the brown sugar evenly over the bottom.

Step 4: Assemble the rest of the cake

Dole Pineapple Upside Down Cake in skilletNancy Mock for Taste of Home

Arrange the pineapple rings over the brown sugar. You want a ring of nine overlapping rings with one ring placed in the center. Place a maraschino cherry in the center of each pineapple ring. Spread the cake batter evenly over the pineapple rings in the pan.

Place the skillet in the oven, with a baking sheet on the lower rack to catch any drips. Bake the cake for 45 minutes.

Step 5: Flip the cake

Dole Pineapple Upside Down CakeNancy Mock for Taste of Home

When the cake is done, run a knife around the outside edge of the cake. Center a large cake platter over the top of the skillet. Wearing oven mitts, carefully flip them over to unmold the cake onto the platter—and be careful not to burn yourself on the sugary syrup from the cake and skillet.

Allow the cake to cool completely, then slice and serve.

The Verdict

Dole Pineapple Upside Down CakeNancy Mock for Taste of Home

It’s a classic for a reason! There was nothing not to love about this original recipe. It came together easily and quickly, and it was supremely satisfying to flip over the cake and reveal the beautifully-arranged top.

Pineapples cooked in brown sugar and butter are pretty dang delicious and the cake was yummy too, tender and sweet under the caramelized topping. If you’ve never tried it before, make 2022 the year of your first pineapple upside-down cake! It’s an iconic dessert recipe that looks lovely on the table no matter the time of year.

How to Serve and Store the Cake

Any leftover cake should be covered with plastic wrap—you can insert a few toothpicks in the top of the cake first to keep the plastic wrap from sticking to the pineapple and cherries.

Store the cake in the fridge for up to three days. You can let the cake come to room temperature before serving, but the slices are also tasty when they’re cold.

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Nancy Mock
Discovering restaurants, tasting bakery treats, finding inspiration in new flavors and regional specialties—no wonder Nancy loves being a food and travel writer. She and her family live in Vermont and enjoy all things food, as well as the beautiful outdoors, game nights, Avengers movies and plenty of maple syrup. Find Nancy’s writing and recipes at her website: Hungry Enough To Eat Six.