Grilled Pineapple Upside Down Cake


I would have missed out on a great cake had I junked this month’s mailer from my electric co-op along with the Blair catalogs and offers from Mutual of Omaha. There’s little in the communiqué on rural electrical matters that interests me, but I’m a sucker for a page of recipes, so I always read the “Let’s Eat” column. A truncated version of the recipe below was included, and I had to try it after reading that it required fresh pineapple – grilled, no less.

Why don’t more recipes for pineapple upside down cake incorporate fresh fruit over canned? The result is infinitely tastier. In the original recipe, slices of pineapple are cooked on a charcoal grill. I got the same effect using a stovetop grill pan, without the smoke and bother. Serve this warm from the oven, but don’t put the knife in the sink just yet. You’ll want seconds.

Grilled Pineapple Upside Down Cake, adapted from a recipe printed in the October 2015 issue of Arkansas Living magazine, a publication of the Electric Cooperatives of Arkansas. Original source for the magazine’s recipe: Big Butts BBQ in Leachville. It is what it is.


1 fresh pineapple, peeled, cut into 1/2-inch slices, and cored. Reserve 6 rings for the cake.

4 tablespoons unsalted butter, melted – divided use

1/2 cup light brown sugar, packed

1/4 cup heavy cream

1/2 teaspoon ground cinnamon


1 cup cake flour

1 teaspoon baking powder

1/4 teaspoon baking soda

1/2 teaspoon table salt

2/3 cup buttermilk

2 large eggs, room temperature

1 teaspoon rum extract (Optional, but I used it and liked the flavor.)

1/2 teaspoon vanilla extract

8 tablespoons unsalted butter, room temperature

3/4 cup granulated sugar

Equipment: a seasoned, 12-inch cast-iron skillet and an electric hand-mixer

[Note: If you prefer a thicker cake, try baking this in a 9- or 10-inch skillet. Also, get as fancy as you want with the pineapple slices. Have the rounds intertwine, or chop up the fruit and cover the bottom of the pan with it.]

Preheat the oven to 350°F., with a rack in the center.

Heat a grill pan on the stovetop over medium heat. Place 6 rings of fresh pineapple in a single layer on a baking sheet or large plate. Brush one side of each ring with melted butter, and place them in the hot grill pan, butter-side down. Brush the tops with melted butter, as well, using a total of about 2 tablespoons. Cook until the undersides of the pineapple are striped with golden brown grill marks. (Watch carefully so that they don’t burn!) Turn to grill the tops. Return pineapple rings to the baking sheet, and set aside.

To make the topping, heat a 12-inch cast-iron skillet on the stovetop over medium heat. As it heats, add the remaining 2 tablespoons melted butter, along with the brown sugar, heavy cream, and cinnamon. Stir to combine thoroughly. Cook until the sugar melts and the mixture begins to bubble. Remove from heat, and arrange the grilled pineapple rings in the bottom of the pan. Cut the last ring to fit in the center, as necessary.

In a small bowl, whisk together the cake flour, baking powder, baking soda, and salt. In a large liquid measuring cup, beat together the buttermilk, eggs, and extracts of rum and vanilla.

In a large bowl, beat together the softened 8 tablespoons of butter and 3/4 cup granulated sugar until fluffy, using an electric hand-mixer on high speed. Scrape the beaters and sides of the bowl to make sure the butter and sugar combine evenly. Add a third of the flour mixture, followed by half of the buttermilk mixture. Repeat, ending with the last third of the flour mixture, beating just until combined. Scrape the beaters and sides of the bowl to ensure that all of the ingredients are incorporated. Spoon the batter into the skillet over the pineapple rings and topping mixture.

Bake at 350°F. for about 45 minutes, or until the cake tests done. Remove the skillet to a trivet or the stovetop, and let cool for about 10 minutes. Place a large serving plate upside down over the skillet, grip the two together with pot holders, and flip them so that the cake drops onto the plate, pineapple side up.

Slice and serve while warm. Do the happy dance. Get seconds. Have the rest for breakfast.

Getting grill marks on the pineapple rings

2 Comments Add yours

  1. S. says:

    This looks delicious. Unfortunately my iron skillet is in pretty bad shape (rusty, yucky, beyond repair). What would you suggest I use in its place to make this yummy looking cake?!?

    1. cookbookwall says:

      Hi, S. I got all sciencey here and poured water into my 12-inch skillet and did the same with a glass 9×13-inch baking dish. The skillet holds 12 cups of water, and the baking dish holds just over 11 cups. This cake doesn’t bake very high, so I think you could make the recipe in a 9×13 pan, too, although I’m not sure how well the glass would release the sticky topping and pineapple. A well-seasoned cast-iron pan is non-stick. I think your rusty skillet is worth saving! A few SOS pads and some elbow grease would do the trick, and re-seasoning is easy. We could make it a dinner party project! For B and J!

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