Pineapple Upside-Down Cake Recipe | Cook the Book

Caroline Russock

Pineapples are not a fruit that I think about on a regular basis. I have nothing against them but they've never been part of my regular fruit rotation and anyone who witnessed me struggle to pick out a ripe one at the market today can attest. You see, I stood in front of the mountainous pile of pineapples for a solid five minutes staring blankly, trying to remember any shred of pineapple knowledge that might be hidden deep in the recesses of my brain. I finally decided that smell was as good a judge as any and went about smelling a good portion of the pineapples. Eventually I found one that smelled, well, like a pineapple, threw it into the cart and made my way home to attempt a very unlikely dessert.

When I saw a recipe for Pineapple Upside-Down Cake in Ad Hoc at Home by Thomas Keller I must admit that I was a bit taken back. This was not the kind of refined, elegant dessert that I expected to see from such a lauded chef. To me pineapple upside-down cake means syrupy canned pineapple slices, glowing red maraschino cherries, and lots of gloopy cake batter made from a boxed mix, purely 1960s housewife stuff. But once I got to reading through the recipe it became clear that this isn't all that different from a tarte tatin, caramelized fruit baked underneath a layer of sweet pastry or in this case, cake.

Of course there are no cans of Dole pineapple rings in Keller's version, and no jarred cherries for that matter. Keller uses fresh, sweet-tart pineapple layered on top of what her refers to as a "schmear", a mixture of vanilla and rum scented butter and brown sugar. The "schmear" is sprinkled with a touch of kosher salt and then topped with carefully placed slices of pineapple. The cake batter is layered on top and the cake is baked until the top is golden and the "schmear" caramelizes the pineapple and bubbles up around the edges.

Once the cake cooled enough to be inverted I ran a knife around the edges and flipped it over to reveal perfectly caramelized spices of pineapple coated with a golden glaze of rum infused goo. I sliced into the cake and was thrilled to see that the pineapple had not been cooked into mush, the slices still had plenty of texture and retained a tart tanginess.

There was nothing kitschy or dated about this cake, the flavors were complex and totally cohesive, delicious and surprising. For what ever reason pineapple upside-down cake has fallen out of fashion, I think that it's about time to bring it back.

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Recipe Facts

Total: 0 mins
Serves: 8 servings

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  • Pan Schmear
  • 8 tablespoons (1 stick; 4 ounces) unsalted butter, at room temperature
  • 1 1/2 tablespoons honey
  • 1/2 teaspoon dark rum
  • 1 cup packed dark brown sugar
  • 1/4 teaspoon pure vanilla extract
  • Kosher salt
  • 1 Gold (extra sweet) pineapple
  • Cake
  • 1 1/2 cups cake flour
  • 2 teaspoons baking powder
  • 8 tablespoons (1 stick; 4 ounces) unsalted butter, at room temperature
  • 1/2 cup plus 2 tablespoons granulated sugar
  • 1/2 teaspoon pure vanilla extract
  • 2 large eggs
  • 1 tablespoon plus 1 teaspoon milk


  1. Preheat the oven to 350°F.

  2. In the bowl of a stand mixer fitted with the paddle, combine the butter, honey, rum, brown sugar, and vanilla and beat until smooth and well blended. Spread 1/3 cup of the schmear over the bottom of a 9-inch silicone baking pan. Sprinkle lightly with salt. (The remaining schmear can be refrigerated for up to 2 weeks or frozen for up to 1 month; bring to room temperature before using.)

  3. Cut the top and bottom from the pineapple and cut away the peel. Cut the pineapple lengthwise into quarters, and cut off the core from each section. Cut each piece into 1/8-inch-thick slices. Beginning at the perimeter of the pan, make an overlapping ring of pineapple slices with the curved side facing out. Make a second ring inside the first one, overlapping the slices in the opposite direction, working toward the center of the pan. Reserve any extra pineapple for another use.

  4. Sift the flour and baking powder together; set aside.

  5. Put the butter and sugar in the bowl of a stand mixer fitted with the paddle and mix on low speed to combine, then beat on medium speed for about 3 minutes, until light and creamy, stopping to scrape down the sides as necessary. Mix in the vanilla. Add the eggs one at a time, beating until the first one is incorporated before adding the second and scraping down the sides as necessary. Beat in the milk. Add the flour mixture in 3 batches, beating until just combined.

  6. Pour the batter into the pan and spread over the pineapple. Bake for 15 minutes. Rotate the pan for even browning and bake for another 20 to 25 minutes, until a cake tester or wooden skewer inserted in the center of the cake comes out clean. Cool the cake in the pan on a cooling rack for 20 to 30 minutes.

  7. Run a knife around the edges of the cake, invert onto a serving platter, and serve warm. (Leftover cake can be stored at room temperature for up to 2 days.)