with Greg Patent, Award Winning Cookbook Author

Fresh Pineapple Upside-Down Cake

What to bring for dessert to Thanksgiving dinner with friends on the island of Kauai? Last year I made a chocolate cream pie, do I repeat or bake something different? Meeting up with a gorgeous, fully ripe pineapple decided it for me: Pineapple Upside Down Cake.

Pineapples originated in South America but became an economic staple in Hawaii by the early 1900s.  James Dole’s modern machinery made it possible for his company to peel, core, and slice about 100 whole pineapples a minute.

In 1926, Dole sponsored a pineapple-cooking contest. Over 60,000 entries poured in, and pineapple upside-down cake accounted for about 2,500 of them.

What this means is that the recipe had originated earlier. Sylvia Lovegren, in Fashionable Food: Seven Decades of Food Fads (1995), says that in 1924, a Mrs. Sidney E. Goodwin gave a recipe for the cake titled Pineapple Glacé in a Seattle charity cookbook. As far as I know, no earlier version has yet turned up in print, but I wouldn’t be a bit surprised if one should at some point.

Though the cake is usually made with canned pineapple, you’ll get a far better dessert with the fresh fruit.

A pineapple will not get any sweeter once picked because it has been cut off from its sugar source. The fruit will get softer, but that’s it. To see if a pineapple will be full of sweet flavor, hold the base of the fruit close to your nose and inhale deeply. It should have a definite fruity smell of pineapple and make you say “aah.” This is the most reliable way I know to determine a pineapple’s ripeness. Refrigeration dulls the aroma, so make sure the fruit you test is at room temperature.

The cake batter itself is a dream to make because there’s no creaming step. You simply melt the butter in a large saucepan and whisk in everything else.

Pineapple Upside-Down Cake

Traditionally this cake is baked in a cast-iron skillet. Lacking such a pan in our condo, and needing to make a dessert that serves 12, I broke with convention and used an ovenproof glass 13 x 9-inch pan and upped the quantity of topping and cake ingredients by half.

1 ripe fresh pineapple 


6 tablespoons (3/4 stick) unsalted butter

1 cup + 2 tablespoons firmly packed brown sugar, light or dark


2 1/4 cups all-purpose flour, spooned into the cups and leveled

1 ½  teaspoons baking powder

1/4 teaspoon baking soda

1/4 teaspoon salt

8 tablespoons (1 stick) unsalted butter

1 cup granulated sugar

3 large eggs, at room temperature

2 teaspoons pure vanilla extract

¾ cup + 2 tablespoons buttermilk

For the pineapple, cut the crown and bottom off the fruit and stand the fruit upright. Use a sharp knife to cut strips of peel off the fruit in a downward motion. Remove any “eyes” (bits of peel indented in the fruit) with a paring knife.

Cut the fruit vertically in half, then cut each half vertically into quarters. Cut away the cores, and set them aside to munch on later for a sweet and juicy treat. Cut each section of fruit crosswise into ½-inch-thick slices.

Adjust an oven rack to the center position and preheat the oven to 325 degrees. Put an empty 13 x 9-inch oven-proof glass baking pan in the oven as it preheats. The pan must be hot to receive the topping or the topping will harden and not be spreadable.

For the topping, melt the 6 tablespoons butter in a medium-size skillet over medium heat. Add the brown sugar, and cook and stir with a wooden spoon until thick and bubbly and the sugar has almost dissolved. Some granules are okay.

Remove the pan from heat. Take the glass pan out of the oven—be careful, it’s hot—and set it on a potholder. Pour the hot topping into the pan and spread quickly with the back of a spoon to make an even layer.

Carefully arrange pineapple pieces close together onto the topping, pressing the pieces in. You may have some extra pineapple. Just eat them for a snack. Set pan aside while you make the cake batter.

For the cake, put the flour into a large bowl and whisk in the baking powder, baking soda, and salt.

Melt the butter in a heavy saucepan over medium heat. When bubbling, remove the pan from the heat and whisk in the granulated sugar.  Add the eggs and whisk until smooth.  Whisk in the vanilla and buttermilk.

Add the liquid to the dry ingredients and stir gently with the whisk (don’t whisk briskly) to make a smooth batter.

Scrape the batter over the pineapple and smooth the top.  Bake 30 to 35 minutes, until the cake is golden brown, it springs back when gently pressed, and a toothpick inserted into the center comes out clean.  Cool the cake in its pan for 1 minute.  Run a small sharp knife around the sides of the cake to release it, cover the cake with a serving platter, and invert the two. Let stand about 30 seconds, then carefully lift off the cake pan. If pieces of fruit have shifted, just move them back in place.

Serve warm or at room temperature.  Cut into portions with a sharp knife. This cake is best when very fresh.

Makes 12 servings.

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