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!
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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.
Nancy 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
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Stand Mixer
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Round Cake Platter
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- 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
Nancy 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
Nancy 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
Nancy 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
Nancy 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
Nancy 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
Nancy 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.
Recipes Inspired By Pineapple Upside-Down Cake
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Pineapple Upside-Down MuffinsFor a modern version of upside-down cake, we use pineapple and a sweet batter to make fun muffins with a cherry on top. —Suzeanne Longwill, Ortonville, Michigan
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Tropical Quinoa Breakfast BowlI have been making this quinoa, coconut, pineapple and mango dish since I was in high school. To make it even more tropical, add some diced papaya.—Billy Hensley, Mount Carmel, Tennessee
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Skillet Pineapple Upside-Down CakeFor a change of pace, you can substitute fresh or frozen peach slices for the pineapple in this old-fashioned recipe. —Bernardine Melton, Paola, Kansas
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Pineapple-Coconut SmoothieUse fresh or frozen fruits in this coconutty recipe. It's like a pina colada, but better for you and more versatile. —Gunjan Dudani, Bellevue, Washington
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Taste of Home
Cranberry Pineapple Upside-Down CakeBoth kids and grown-ups like this gorgeous dessert. It'll keep a few days and is actually better the second day, so you can make it a day ahead. —Sherry Conley, Noel Hants County, Nova Scotia
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Pineapple Upside-Down Dump CakeNo matter the season, this dump cake recipe is wonderful! It works well with gluten-free and sugar-free cake mixes too. —Karin Gatewood, Dallas, Texas
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Taste of Home
Pina Colada Grilled PineappleDuring a cookout with friends, I forgot about dessert. I had a fresh pineapple and coconut, so I improvised. Now I grill pineapple at every cookout. —Josee Lanzi, New Port Richey, Florida
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Pineapple Cheesecake-Topped CakeMy brother-in-law asked me to make a cheesecake version of pineapple upside down cake, and after many attempts, I created one. It’s a yummy twist on a classic.—Rebecca Everett, Kansas City, Missouri
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Classic Pineapple Upside-Down CakeA classic recipe like this never goes out of style! It’s delicious with the traditional pineapple, but try it with peaches or a combination of cranberries and orange. —Bernardine Melton, Paola, Kansas
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Pineapple OatmealOatmeal for breakfast is a standard item, but I like to mix it up a bit. This version gets some natural sweetness from pinapple juice and tidbits. It is definitely worth trying! —Maria Regakis, Somerville, Massachusetts
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Taste of Home
Spiced Pineapple Upside-Down CakeI often bake this beautiful cake in my large cast-iron skillet and turn it out onto a pizza pan. —Jennifer Sergesketter, Newburgh, Indiana
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Tropical MuffinsI entered these muffins at our county fair and won the grand champion award for baked goods. They're so moist, they don't need butter. —Sylvia Osborn, Clay Center, Kansas
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Pineapple Upside-Down Cake for TwoTender, moist and sweet, these two luscious but lighter cakes are as special as the person you choose to share them with! —Taste of Home Test Kitchen
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Tropical Compote DessertTo make a more adult version of this recipe, use brandy instead of the extra tropical fruit juice. —Taste of Home Test Kitchen
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Pineapple Upside-Down CupcakesI have baked cupcakes for years. These easy to make treats make an attractive dessert for special occasions. —Barbara Hahn, Park Hills, Missouri
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Taste of Home
Grill up fresh peaches and pineapple slathered in cinnamon butter and use them to make a refreshing summer sangria. I also like to add slices of grilled lemon and lime to drop in the glass for a citrusy boost of flavor. —Heather King, Frostburg, Maryland
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Makeover Pineapple Upside-Down CakeBoth of my boys loved this makeover version of a family favorite, and even my husband, who is a bit picky, wants a piece in his lunch tomorrow! —Mary Lou Moeller, Wooster, Ohio
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Taste of Home
Pineapple Colada ShakeThis frothy, refreshing coconut and pineapple shake is sinfully delicious! Cool and creamy, it just begs to be your poolside companion. —Melissa Jelinek, Menomonee Falls, Wisconsin
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Pineapple Sheet CakeThis sheet cake is perfect for serving to a crowd. It keeps so well that you can easily prepare it a day ahead and it will stay moist. I often bring it to church potlucks, and I have yet to take much of it home. —Kim Miller Spiek, Sarasota, Florida
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Taste of Home
Pineapple Upside-Down CheesecakeMy mom often made pineapple upside down cake, but I prefer something creamier. This recipe looks just like her cake, but gets even tastier as pineapple upside down cheesecake. —Marilyn McGinnis, Citrus Heights, California
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Taste of Home
Easy Pineapple Upside-Down CakeHere's a traditional recipe for pineapple upside-down cake that's been updated with packaged items for convenience. —Karen Ann Bland from Gove, Kansas
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Mini Pineapple Upside-Down CakesThese individual pineapple upside-down cakes are an eye-catching addition to my holiday dessert table. A boxed cake mix makes them easy to bake anytime. —Cindy Colley, Othello, Washington
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