This 100-Year-Old Award-Winning Cake Is Still a Keeper

Pineapple rings aren't just for brown sugar baked ham, edible fruit arrangements, and wearing as pretend eyeglasses. After a scratch-baked banger swept the competition in a Dole recipe contest back in 1925, pineapple upside down cake entered the chat—and it stuck around for decades. Bust out the cocktail umbrellas—it's a party in a pan!

Pre-cut, peeled, cored, and ready to rock, the Hawaiian Pineapple Company (later Dole) popularized canned pineapple rings in 1913. And it appears that around the same time, American home bakers were completely over regular side-up cake. Just like Medieval Europeans and the post-Marie Antoinette French were already doing with flipped-over apple tarte Tatin, fruit landed in the baking dish first, followed by cake batter. And, since cat memes had yet to become a thing, people went nuts for this mind-bending presentation.

Trouncing an reported 60,000 entries for Dole's recipe contest (2,500 were other variations on pineapple upside down cake), Norfolk, Virginia's Mrs. Robert Davis created the future icon of retro bakes—a tender, not-too-sweet cake finished with a melt-in-your-mouth, pineapple and cherry-studded topping. 

How to Make Dole's Original 1925 Pineapple Upside Down Cake

Modern pineapple upside down cake recipes often skip the ingredients that I think take this vintage original over the top: lemon zest, lemon juice, and sour cream, which lend a moist, tender crumb. Even if you've never sampled the O.G., those whose grandmothers made it say Dole's Original 1925 Pineapple Upside Down Cake takes them right back to their favorite childhood treat.

First, make the pineapple layer. Reserving two tablespoons of liquid, drain the pineapple slices, and then separate the egg yolks from the whites, and zest and juice the lemon. In a 10-inch cast-iron skillet, melt half of the butter, then stir in the brown sugar until combined. Take the pan off the heat, spread the mixture evenly over the bottom, and place the pineapple slices into the pan. Add a cherry to the center of each ring.

Next up is the cake: In a medium bowl, use an electric mixer to beat the rest of the butter and granulated sugar. Then, beat in the egg yolks, lemon juice, lemon zest, and vanilla. In a small bowl, mix the flour, baking soda, and salt. Slowly add the dry ingredients to the wet ingredients, mixing at low speed, alternating portions with the sour cream and reserved pineapple liquid. 

Beat the egg whites on high until they get soft, droopy peaks, then beat in the granulated sugar until you get a stiff meringue you can safely hold upside down. Fold the meringue into the batter, then pour over the pineapples in the pan. Bake at 325 degrees Fahrenheit for about 35 minutes, and a cake tester comes out clean. Let the cake cool for about 10 minutes before flipping it onto a platter.

I baked my cake in a nine-inch springform pan (with a baking sheet underneath to catch the drips), then inverted it onto a 10-inch cast iron pan for the rustic look. However you bake it, flipping the cake onto any serving dish that contains the extra syrup will do!

Nothing beats a slice of cake that's still warm from the oven. But I can confirm this century-old taste of history is also fridge-fabulous—and maybe even better when chilled. I'm practically fainting in my Roaring Twenties ostrich feather lounging robe just thinking about those chewy caramelized edges. If you love nostalgic recipes that stand up to generations of taste-testing without changing a thing, Dole's Original Pineapple Upside Down Cake is calling your name.