Best-Ever Pineapple Upside-Down Cake - No. 117

The cozy classic with a Hawaiian past just got a better batter

We’ve been revisiting cast iron in May with fried chicken and cornbread and now pineapple upside-down cake. This isn’t your typical upside-down cake, but I hope by now you know not to expect the usual from me. And read on down for some news on audio coming to Between the Layers! Plus, the results of last week’s Cornbread Survey.

Pineapple upside-down cake made with canned pineapple. Photos by Danielle Atkins

PINEAPPLE UPSIDE-DOWN CAKE BRINGS SMILES when it comes out of the oven. And you have to admire how it was created with just a simple can of pineapple.

But what makes this cake stand out is what you don’t see…the sticky, buttery stuff on the bottom of the skillet. And once flipped upside-down, it looks phenomenal, even if some bits of pineapple cling to the pan and you have to patch those back together.

I’ll go so far as to say it’s one of our more comforting cakes, the cozy slippers of the confectionery department. And it came on the scene in 1925, when the Hawaiian Pineapple Company, what became Dole Food Co., staged a recipe contest asking cooks to submit their best recipe with canned pineapple and received 2,500 recipes for pineapple skillet cake. Not one or two…2,500!

Harvesting pineapples on a pineapple plantation in Hawaii sometime between 1910-1925. Photo by HUM Images/Universal Images Group via Getty Images

Hawaiian pineapple, said the early Dole ads, was distinctive for "its beautiful golden color, in texture, in flavor, in ripeness, in digestive and tonic properties."

Baking with tropical flavors like pineapple, an ingredient you couldn’t grow in your backyard, was an easy upgrade, much like adding blood orange or Meyer lemon today. And everyone was crazy about pineapple upside-down cake, according to the food columnist of the Lincoln Evening Journal in Lincoln, Nebraska, in 1930:

"If one could speak of a dessert taking the country by storm, it would certainly apply to pineapple skillet cake, known also as pineapple upside-down cake."

Before the pineapple upside-down cake, pineapples signaled status, power, and wealth. As people tried unsuccessfully to grow the fruit in chilly climates, they desired them even more.

So named because it resembled a pine cone. The Smooth Leaved Green Antigua Pine, 1807. Artist Henri Merke. Photo by Heritage Art/Heritage Images via Getty Images

Pineapples are a member of the Bromeliad family and are indigenous to present-day Brazil and were cultivated throughout Central and South America. Natives of these New World lands would place fresh pineapples outside their homes as a sign of friendship. To them, the pineapple was food, medicine, and the leaf fibers could be spun into cloth.

The Spanish introduced the pineapple to Europe, where it became a symbol of hospitality and wealth. When the English colonists arrived pineapple-obsessed in America, they imported pineapples from the West Indies and displayed them in the center of the table for dinner guests. Pineapples were carved into wood and stone, styled from silver and brass, and were painted onto wallpaper and fine china.

According to historian Francesca Beauman in her book, The Pineapple: King of Fruits, George Washington first tasted pineapple while visiting Barbados and was enamored with it. And Thomas Jefferson's kitchen prepared a pineapple pudding, but ever the epicure and gardener, Jefferson marveled at the specimen of pineapple and was reluctant to slice into it.

Queen Lili'uokalani, Hawaii's last monarch, overthrown in 1893.

Hawaii, empire building, the pineapple industry, a deposed queen, and eventually, statehood.

After the Spanish introduced pineapple to Hawaii, the fruit flourished in the tropical climate. In 1899, an entrepreneur, James Dole, returned to Hawaii to visit his cousin, Sanford Dole, an attorney advocating for the westernization of Hawaii.

Outside of college education back East, the Dole cousins spent their lives in Hawaii and were the sons of New England missionaries to Hawaii. James Dole created the equipment to peel, cut, and pack canned pineapple and grew Dole pineapple into the world’s largest pineapple packer.

Sanford Dole grew political connections that after a coup to overthrow Queen Lili’uokalani, the last native Hawaiian monarch in 1893, placed him in the governor’s seat of the new republic. Hawaii became the 50th U.S. state six decades later, on August 21, 1959.

Pineapple had found its way into our ice cream, pudding, pie, cake, and cocktail recipes. In 1993, the U.S. government formally apologized to native Hawaiians for overthrowing their kingdom 100 years earlier.

Joan Namkoong, born and raised in Hawaii and former food editor for the Honolulu Advertiser, said Hawaiians today still bake pineapple upside-down cake.

But Dole hasn’t harvested Hawaiian pineapples since the 1980s when production moved to Thailand, Ecuador, Costa Rica, Honduras, the Philippines, and the Ivory Coast.

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Pineapple upside-down baked with fresh pineapple.

Making the best pineapple upside-down: A hot milk sponge cake is the secret

Today, in the midst of so many crises—an infant formula shortage, the Russian invasion of Ukraine, inflation at our doorstep, world hunger, Covid anxiety, and dissatisfaction with the status quo—why write about the imperialism of pineapple and upside-down cake?

To open our eyes. Plus, we need a little comfort.

But honestly, I was never a pineapple upside-down devotee because the cake was invariably dry and didn’t match up to the fruit, butter and sugar topping. Oh sure, it was great right out of the oven, but hours later, a day later, it was meh. Or the recipe was too complicated because you had to separate the egg yolks and beat the whites and fold them in.

And then I remembered hot milk sponge cake, an old recipe popularized when baking powder cakes came into vogue. A moist cake. Easy, too.

So I used that method in making a pineapple upside-down cake, and what resulted was a soft and glorious cake every bit as good as the caramelized pineapple nestled in the skillet.

And you can use other fruit, too, in this recipe. As we go into summer, absolutely use strawberries or PEACHES!

Bake this cake for Memorial Day and summer get-togethers and birthdays. It’s a stand-out with a complicated past, but it couldn’t be easier to love.

Mahalo. - xo, Anne

What do you love about pineapple upside-down cake? Any memories?

Substituting 2 to 3 cups sliced strawberries for the pineapple in an upside-down.

Coming Thursday for Paid Subscribers

In my first audio segment on Between the Layers, I tell the story of a very special lunch I made with Julia Child in her home kitchen in Cambridge, Massachusetts, in August of her 80th year. You can play it while you walk or are in the car or in the kitchen. I’ve been gifted a wonderful career filled with food memories and experiences, and I begin sharing these one Thursday a month.

Do you have questions about subscribing? I will admit some aspects of Substack are confusing. Email me, and let’s see if I can help. And if you’d like to subscribe but cannot afford it, email me (anne@annebyrn.com).

The Cornbread Survey Results!

As of this writing, 236 of you took part in my Cornbread Survey. Thank you! Based on your replies, here are the results:

• More than three-quarters of you—76 percent—bake yellow cornbread, followed by 21 percent who make white. A few bake both, and a couple bake blue.

• Sweet vs. Non-Sweet was divided right up the middle, with the no-sugar in my cornbread camp barely edging out sweet 52 to 48 percent. It was close!

• As for fat, it’s butter and vegetable oil in cornbread in a tie. The rest of you use bacon grease, lard, Crisco, olive oil, or a butter substitute.

• Your secrets to making great cornbread were profound! The most suggested tips were high heat, hot skillet, cast iron, buttermilk, and my favorite: Bake it with love.

• As for where you learned to make cornbread, the responses were all over the place. From Washington State to Florida, to northern Illinois, to rural Georgia, to western Pennsylvania, to Montana, to Salt Lake City, to West Virginia coal mining country, to Baton Rouge, to Maine, to Minnesota, to Hawaii, where the cornbread is sweet. Invariably, people learned to make cornbread from a family member, a mother, a grandmother, or from 4-H classes. A reader who lives in Ohio but grew up in Virginia said there was an old gristmill on their farm that produced the best stone-ground fine white cornmeal.

THE RECIPE:

My Favorite Pineapple-Upside Down Cake

This cake has seen a lot of variations through the years, whether flavoring the batter with lemon zest or almond extract or swapping out canned pears or sauteed apples for the pineapple. And it might have been once a yeast cake, as New York Times food editor Clementine Paddleford claimed the original pineapple upside-down was first baked by Jewish bakers in Chicago long before the 1920s. You can use fresh or canned pineapple in this recipe. And don’t be concerned that the batter is runny. You do need a 12-inch cast iron skillet, so measure your skillet from top rim to rim. If you have a smaller skillet, you can still make this cake, but you’ll need to bake it in two smaller skillets.

Makes 12 to 16 servings

Prep: 30 to 35 minutes

Bake: 40 to 45 minutes

Topping:

1 ripe pineapple (about 2 to 3 pounds), or 1 can (20 ounces) pineapple slices packed in juice, about 10 slices, and 10 maraschino cherries, optional

6 tablespoons unsalted butter

3/4 cup light brown sugar, firmly packed

Cake:

1 cup whole milk

4 tablespoons (2 ounces; 1/2 stick) unsalted butter

2 teaspoons vanilla

2 cups granulated sugar

4 large eggs

1/3 cup vegetable oil

2 cups unbleached all-purpose flour

2 teaspoons baking powder

1 1/4 teaspoons salt

1. Preheat the oven to 350 degrees F. Cut the top off the pineapple, slice off the peel, quarter it lengthwise, and remove the core. Cut the pineapple quarters into 3/8-inch crosswise slices, and set them aside.

2. Place the butter in a 12-inch skillet over medium heat to melt, about 2 minutes. Stir in the brown sugar until the mixture bubbles, about 4 minutes. Pull the skillet off the heat. Arrange the pineapple slices in concentric circles on top of the butter and sugar, beginning at the edges of the pan and overlapping the pieces slightly. Set the pan aside. You can sprinkle ground cinnamon or drizzle lavender honey or dark rum on the pineapple slices before pouring the cake batter over, if desired.

2. For the cake, place the milk and butter in a small saucepan over medium heat until the butter melts, about 2 minutes. Stir in the vanilla and set aside. Place the sugar and eggs in a large mixing bowl and beat with an electric mixer on medium speed until the mixture is thick and lemon colored, 2 to 3 minutes. Add the oil and blend to combine. Set aside.

3. Place the flour in a small bowl, and stir in the baking powder and salt. Alternately add the flour mixture to the egg and sugar mixture with the hot milk mixture, beginning and ending with the flour and beating on low speed until smooth. The batter will be runny. Pour the batter over the pineapple in the skillet, and place the pan in the oven.

4. Bake until the cake is golden and tests done by lightly pressing on the center of the cake, about 40 to 45 minutes. It should spring back. Remove the skillet from the oven, and let the cake rest in the skillet for 5 minutes. Run a knife around the outside of the pan to loosen it. Place a flat platter, board, or plate over the skillet and invert the skillet so the pineapple is right-side up. Replace any pineapple still stuck to the bottom of the skillet. If desired, drizzle the top of the cake with dark rum.

5. Serve warm, or let the cake cool 30 minutes, then slice and serve with whipped cream, if desired.