Pineapple Upside-Down Cake
Prep time
Cook time
Total time
An American classic, Pineapple Upside Down Cake became famous as the result of a 1925 contest conducted by the Dole Company; however food historians suggest the recipe is much older. Early recipes often refer to this recipe as a “skillet cake” as people used a heavy skillet, such as a cast iron skillet, to cook the cake on top of the stove instead of in an oven. Even today, using a cast iron skillet is the traditional method for preparing and baking an upside down cake; the butter and brown sugar can be heated directly on the stove and the heavy iron helps caramelize the butter and sugar while baking.

Original recipe versions have pineapple and cherries only on top of the cake. I believe the cake is prettier with extra pineapple and cherry halves placed around the outer edge, along with a few pecan halves for a finishing touch. Pineapple Upside Down cake is wonderful when served still warm from the oven with a big dollop of sweetened whipped cream.
Recipe type: Dessert | Upside-Down Cake
Serves: 8 to 10
  • 10 or 12 pineapple slices, packed in unsweetened pineapple juice
  • 10 or 12 maraschino cherries
  • ¼ cup unsalted butter
  • ⅔ cup firmly packed light brown sugar
  • 2 tablespoons reserved pineapple juice
  • ¼ cup pecan halves
Tip: You may use fewer pineapple slices and cherries if you prefer, and depending on the size of your pan. I used 12 pineapple slices for this cake, 7 for the top and 5 cut in halves to ring the outer edge. But you can also see photos below using just 10 pineapple slices. One 20-ounce can normally contains 10 pineapple slices.
  • 1½ cups sifted cake flour
  • 2 teaspoons baking powder
  • ¼ teaspoon salt
  • ½ cup milk (preferably whole milk)
  • 1 teaspoon pure vanilla extract
  • ⅓ cup unsalted butter, room temperature
  • ⅔ cup granulated sugar
  • 2 large eggs
Preheat oven to 350 degrees F. Use one 10-inch cast iron skillet. You can substitute any heavy 10-inch ovenproof skillet with an ovenproof handle, or a 9-inch or 10-inch round or square cake pan, or a 10-inch springform pan with the outside wrapped in heavy duty foil to prevent leakage.
  1. Drain the pineapple slices and cherries, reserving 2 tablespoons of pineapple juice. Place the pineapple and cherries on paper towels to absorb excess moisture. You will need 7 whole pineapple slices and 7 whole cherries. Slice the remaining pineapple slices and cherries in halves.
  2. In the skillet, melt the butter over low heat. Use a pastry brush to spread a little of the melted butter around the sides of the skillet to help prevent the fruit from sticking after it is baked. When the butter is completely melted, stir in the brown sugar and pineapple juice until thoroughly combined, then continue to heat just until the mixture starts bubbling around the edges to help the sugar fully dissolve; remove from heat. remove from heat. Tip: if you are using a cake pan or springform pan in place of a skillet, then use a small heavy saucepan to melt the butter, stir in the brown sugar and pineapple juice until thoroughly combined, heat just until the mixture starts bubbling around the edges to help the sugar fully dissolve, then pour the hot mixture into a lightly greased cake pan.
  3. Place one whole pineapple slice on top of the brown sugar mixture in the center of the skillet, and six whole slices surrounding it. Place a whole cherry in the center of each pineapple slice. Place the half slices of pineapple side by side against the sides of the skillet with the cut edges down in the brown sugar mixture. Place a half cherry in the center of each half slice of pineapple. Tuck the pecans, rounded side down, into any gaps between the pineapple slices. Set aside. Tip: if using just 10 pineapple slices for this recipe, then place the half slices around the edge of the pan in the space where the whole slices meet.
  4. Pineapple Upside-Down Cake
  1. In a medium mixing bowl, combine flour, baking powder, and salt; sift or whisk together to mix. Set aside.
  2. In a small bowl, stir the milk and vanilla together. Set aside.
  3. In a large bowl of an electric mixer, cream the butter and sugar until light and fluffy. Tip: To cream, start by placing the butter in the bowl, with an electric mixer on medium speed begin by beating the butter about 1 minute until it is smooth and light in color. With the mixer still on medium speed, slowly add the sugar to the butter, either one tablespoon at a time, or in a very slow steady stream, taking from 3 to 5 minutes to add all of the sugar, and beating until the butter and sugar are fully incorporated and the mixture is a light, or pale yellow color, with a fluffy texture. While adding the sugar, stop the mixer occasionally to scrape the mixture off the paddle and scrape down the sides and bottom of the bowl with a rubber spatula so the mixture blends evenly.
  4. Add eggs one at a time, beating until thoroughly mixed. Tip: For each egg, crack the egg into a small bowl and whisk with a fork to thoroughly break up the egg before adding to the creamed mixture. Start with the mixer on low speed so the liquid from the egg doesn’t splatter, once the egg is partially mixed increase the speed to medium. Each egg should be fully incorporated into the mixture before adding the next egg, taking about one minute to blend in.
  5. With the mixer on low speed, add about one third of the flour mixture, mix just until the flour is almost completely blended. Scrape the bowl down, and add about one half of the milk mixture, blending just until mixed. Scrape the bowl down again and continue alternating with the flour mixture and milk mixture, ending with the last portion of the flour, and stirring just until blended.
  6. Pour batter over the fruit in the skillet; use a rubber spatula, back of a spoon, or small offset spaula to spread the batter evenly and smooth out the top.
  7. Bake: Bake 40 to 45 minutes or until the cake is golden brown on top and a long toothpick, wooden skewer, or cake tester inserted in the center comes out clean. Remove the skillet from the oven and place on a wire cooling rack to cool for 5 minutes.
  8. Upside Down: Run a thin kitchen knife around the edge of the skillet to loosen the sides. Invert the skillet onto a serving plate. Leave the skillet in place one or two minutes before lifting to let the syrup drip down onto the cake. Carefully lift the skillet off of the cake. If any fruit has stuck to the skillet, remove and place it back on the cake.
  9. Pineapple Upside-Down Cake
Serving Suggestion:This cake is best when served still warm, along with a big dollop of sweetened whipped cream.
Source: Beranbaum, Rose Levy, The Cake Bible, William Morrow and Company Inc., New York, 1988Cunningham, Marion, The Fannie Farmer Baking Book, Random House, New York, 1984Walter, Carole, Great Cakes, Random House, New York, 1991
Republished 9-23-2018 to update ingredients, instructions, and photos.
Recipe Notes
Pan: One 10" Cast Iron Skillet, or One 9" Round, or One 10" Round, or One 10" Springform Oven Temp: 350° Storage: Covered, Room Temperature

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