My husband usually wants an angel food cake for his birthday. This year he began hinting about changing things up nearly a month in advance. When his request finally came in for pineapple upside-down cake, I cringed a little. After remembering that it was his birthday, not mine, I rose to the occasion and got out several references: Joy of Cooking, The Fannie Farmer Cookbook, and Jennie Schacht’s Farmers’ Market Desserts for a more modern perspective. The cake turned out great on the first try!
baked and resting before the flip
Pineapple Upside-Down Cake
makes one 10-inch cake; adapted from Joy of Cooking and Jennie Schacht's Maui Pineapple-Macadamia Upside-Down Cake in Farmers' Market Desserts
Ingredients
Topping
- 1 20-ounce can pineapple rings, unsweetened
- 7 maraschino cherries, 6 halved one left whole
- 4 tablespoons unsalted butter
- ½ cup light brown sugar, firmly packed
- 2 tablespoons dark rum (optional)
Cake
- 1½ cups all-purpose flour
- 1¾ teaspoons baking powder
- ½ teaspoon Kosher salt
- ½ cup unsalted butter (8 tablespoons/1 stick), softened
- ¾ cup granulated sugar
- 2 large eggs
- ½ teaspoon vanilla extract
- 1 cup whole milk
Instructions
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Preheat oven to 375°F then lower to 365°F when you put the pan in the oven (350°F if you're not at high elevation like Bozeman).
To make the topping:
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Drain 7 pineapple rings on paper towels. Halve 6 maraschino cherries and leave one whole for the center. In a 10-inch cast iron skillet set over moderate heat, melt the butter with the brown sugar and rum, whisking to make a smooth sauce. Remove from heat and arrange the pineapple and cherries to make a pattern you like—it will be the top when you unmold the cake.
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Return the pan to medium heat and cook until the caramel bubbles up around the pineapple, about 5 minutes. Remove from heat and set aside.
To make the cake:
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Whisk together the flour, baking powder, and salt in a bowl and set aside.
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In mixing bowl, cream the butter and granulated sugar until light, about 5 minutes. Mix in the eggs one at a time, stopping mixer to scrape down the sides of the bowl. On low speed, add half the flour bowl, then all of the milk, and then the remaining flour, beating just until combined after each addition.
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Pour the batter evenly over the pineapple in the skillet, filling the perimeter first and working towards the middle to keep the caramel-pineapple layer in place. Smooth the top with a spatula and bake at 365° for about 45 minutes, until the aroma wafts in your kitchen and top is beginning to dry and brown at the edges.
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Set aside to rest for 10 minutes before running a thin blade around the edge and inverting onto a serving plate. If any pineapple rings stick to the pan, simply use a fork and transfer into position.
