Dessert Recipes

Pineapple Upside-Down Cake

pineapple upside-down cake

Our 70th anniversary has everyone in the test kitchen paging through our collective memory and favorite mid-century cookbooks for the food our parents and grandparents loved. Pineapple upside-down cake is the perfect candidate because it’s never really gone out of style, and this particular recipe feels absolutely of the moment — and oh golly, is it good.

Pineapple upside-down cake has actually been around for a while. We could not find a first, but according to food historians, in 1925, the Hawaiian Pineapple Company (now Dole) held a pineapple recipe contest to celebrate their newly minted ring cutter, and garnered 60,000 entries. A whopping 2,500 of them were for upside-down cake! The company parlayed that enthusiastic response into an ad campaign, launching the recipe’s career as a fixture at American parties and bake-sale cakewalks. But its real heyday didn’t come until the 1950s, when supermarkets like Gelson’s started carrying boxed cake mix. It’s kind of, almost, a retro dump cake.

The recipe is a natural for the cast-iron skillet. We’re all a little in love with our skillets at the moment, but people have been making cakes, specifically upside-down cakes, in them since the Middle Ages. It was a matter of fewer pans and unreliable (or nonexistent) ovens in ye olde tymes, but why do it now? Even modern stoves have their foibles: a cast-iron skillet’s superpower is holding heat, so whatever’s happening with your oven temp, you’ll get a nice even bake. They also give cakes a wonderfully crisp exterior, adding unexpected texture to all three sides of the cake. Bonus: the pan’s handle makes it a lot easier to flip the cake.

On that note, we will confess that this recipe includes melting a half stick of butter in the bottom of the cast iron. Trust us, it’s a good idea. It’ll help the cake slide out of the pan, but more than that, it’s part of the cake’s scrumptious magic. We warm the skillet, add the butter, and then take it off the heat and sprinkle on the brown sugar just before we add the fruit and cake batter — so the sugar doesn’t have time to melt. In the oven, the butter and sugar caramelize against the hot cast iron, glazing the pineapples and cherries, and soaking into the crumb. What heaven it is to bite through that sweet layer to the soft, buttery cake!

Pineapple upside-down cake always knocks it out of the park — for a kiddo’s birthday or a splashy lunch with the S.O. If you can manage it, try to save at least one piece for the morning after: upside-down cake is wonderful with coffee. That said, and our own selfish desires set aside, the cake is so unabashedly pretty and cheerful, it’s also the one we like to leave on our BFF’s porch when they’re in need of a little hoorah.

Servings: 8 to 10

Cooking spray, for greasing the pan

1 ⅔ cups all-purpose flour

2 tsp baking powder

¾ tsp kosher salt

2 large Gelson’s eggs, room temperature, separated

1 ½ sticks unsalted butter, room temperature, divided

1 cup granulated sugar

½ cup whole milk, room temperature

1 Tbsp vanilla extract

¾ cup packed brown sugar

1 20-oz can pineapple rings, drained

13 maraschino cherries


  1. Preheat the oven to 350°. Lightly grease a 9” cast-iron skillet with cooking spray.

  2. In a medium bowl, combine the flour, baking powder, and salt. Set aside.

  3. In a small bowl, whisk the egg yolks. Set aside.

  4. In a medium bowl, whisk the egg whites until light and frothy, about 2 minutes. Set aside.

  5. In a stand mixer fitted with the paddle attachment, beat 1 stick of butter until soft and smooth. Then gradually beat in the granulated sugar.

  6. Add the egg yolks and beat until smooth, scraping down the sides of the bowl as needed.

  7. Add the milk and the flour mixture in 2 alternating batches, mixing gently but thoroughly after each addition.

  8. Fold in the beaten egg whites, then the vanilla.

  9. Over low heat, melt the remaining ½ stick of butter in the skillet and then remove from heat. Sprinkle the brown sugar evenly over the top. Space the pineapple rings atop the sugar, and place the maraschino cherries decoratively in the pan. Spoon the batter on top.

  10. Bake the cake for 35 to 45 minutes, or until a toothpick inserted into the center comes out clean.

  11. Remove the cake from the oven. Loosen its edges and let cool for 10 minutes.

  12. Loosen the cake’s edges again, place a serving plate on top of the skillet, and carefully flip the pan over, inverting the cake. Lift the pan off the cake, scraping any remaining pineapple or brown sugar from the pan onto the top of the cake.

  13. Serve the cake warm or at room temperature. Store it at room temperature, well-wrapped, for up to 5 days, or freeze for up to 2 weeks.

Recipe adapted from: King Arthur Baking Company

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