Pineapple Upside-Down Cake

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Pineapple Upside-Down Cake
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Learning to bake a pineapple upside-down cake is practically a rite of passage for young cooks, and an exciting one at that -- making the sweet, gooey topping, arranging the pineapple rings in the pan, then flipping the finished cake.
Although you can make this fruit-topped classic with many different batters, here's one we particularly like: a buttermilk batter with a hint of cinnamon. We've flavored the topping with a secret ingredient too: a bit of maple syrup. Add a big dollop of homemade Mapley Whipped Cream, and it's positively irresistible.
Upside-down cake is often baked in a skillet, but we recommend a 9-inch square cake pan, used here. It holds more fruit than a round pan -- 3 perfect rows, yielding 9 equal slices. Plus, it's a little easier to invert the cake from the square pan (although kids may still need a hand when it's time to turn the cake upside down).
Who invented pineapple upside-down cake? Food historians think upside-down cakes have been around since at least the late 1800s. Some say the first ones were called "skillet cakes" because they were often cooked in pans on top of the stove instead of in ovens, which were heated by wood or coal and could be very unreliable. In 1925, skillet cakes were really catapulted to popularity when the Hawaiian Pineapple Company, today called Dole Food Company, sponsored a cooking contest for recipes that used their canned pineapple slices. When all the submissions were tallied, some 2,500 of them were recipes for pineapple upside-down cake.

What you'll need

  • PINEAPPLE TOPPING
  • 9 canned pineapple rings
  • 4 tablespoons butter
  • 2 tablespoons maple syrup
  • 3/4 cup packed light brown sugar
  • 9 canned pitted cherries, or a handful of dried, sweetened cranberries
  • CAKE
  • 1/2 cup unsalted butter, softened
  • 2/3 cup sugar
  • 2 large eggs, at room temperature
  • 2/3 cup buttermilk, at room temperature
  • 1 tablespoon maple syrup
  • 1/2 teaspoon vanilla extract
  • 1 1/2 cups all-purpose flour
  • 1/2 teaspoon salt
  • 1/2 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/4 teaspoon cinnamon

How to make it

  1. Step 1

    Line a plate with two layers of paper towels and place nine pineapple rings on top to drain. Blot the tops with paper towels too, to remove excess juice.

  2. Lightly butter a 9-inch square cake pan and set it aside. In a small saucepan, heat the butter and maple syrup over medium-low heat. When the butter has melted, stir in the brown sugar with a long-handled wooden spoon. Increase the heat slightly. Stir the mixture until it comes to a gentle boil, then continue cooking it for 30 seconds.

  3. Step 3

    Remove the pan from the heat and immediately scrape the mixture into the buttered cake pan. Using oven mitts (cooked sugar can get extremely hot), tilt the cake pan to evenly coat the bottom.

  4. Step 4

    Using a fork, carefully place the nine pineapple rings in the pan, creating three rows of three. Place a cherry or a few dried, sweetened cranberries in the center of each ring, then set the pan aside.

  5. Position one of your oven shelves in the center and heat the oven to 350 degrees while you make the cake batter. In a mixing bowl, beat the butter with an electric mixer on high speed until fluffy. Gradually beat in the sugar. Add the eggs, one at a time, beating well after each addition.

  6. Step 6

    Measure the buttermilk, then pour the maple syrup and vanilla extract into the same measuring cup. Blend the combined liquids with a spoon. Pour half of the liquid mixture into the creamed butter and sugar and beat well for 30 seconds.

  7. Sift together the flour, salt, baking powder, baking soda, and cinnamon into a mixing bowl. Stir half of the dry mixture into the creamed ingredients. Beat briefly, until smooth. Stir in the remaining buttermilk mixture. Then add the rest of the dry mixture, beating on medium speed until the batter is evenly combined.

  8. Step 8

    Drop heaping spoonfuls of the batter here and there over the pineapple, then smooth the batter with the back of the spoon until it is evenly spread. Bake the cake on the center oven rack for approximately 35 minutes, until the cake is springy to the touch and a wooden toothpick inserted in the center comes out clean. Transfer the cake to a wire rack and let it cool in the pan for 15 minutes.

  9. Step 9

    Now it's time for the exciting part: flipping the cake. Run a spatula or a butter knife down the sides of the cake to loosen it. Then invert a large, flat serving dish (if you don't have one, you can use a baking sheet lined with aluminum foil) over the cake pan.

  10. Step 10

    Wearing long sleeves and oven mitts to protect your arms from any hot drips, hold the dish and cake pan together and invert the cake in one quick motion (a parent's job if the chef is young). Tap the pan on the bottom if the cake doesn't drop right out. Then slowly lift the pan from the cake. If some of the fruit sticks to the pan, simply lift it from the pan with a fork and place it back on the cake. Cool the cake for at least 20 minutes before slicing and serving. Makes 9 servings.

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