For Swan’s birthday, Calla made pineapple upside-down cake, which is not the kind of cake you can put candles on. So, there was nothing to blow and make wishes on. Nobody missed the candles, because you are eating pineapple upside-down cake, there is nothing much left to wish for.”
– Jenny Wingfield, “The Homecoming of Samuel Lake”
This mid-century pineapple dessert was born out of innovation
Pineapple upside-down cake was born out of mechanical engineering and modern ingredients that gave homemakers time to bake a cake that was pretty and tasty.
The dessert evolved from skillet cakes that had been around, in many cultures, for centuries. Cakes cooked over coals in cast-iron pans that featured legs called spiders. As more homes began featuring cast-iron ovens, the pans became flat-bottomed and the term skillet cake was used to describe them. Initially, apples were the most popular ingredient for the cakes. But that changed when an engineer for James Dole, “The Pineapple King,” designed a machine that sliced pineapples into beautiful rings for canning. Sudden and easy access to an exotic fruit made it a natural for this cooking technique. The almost simultaneous creation of maraschino cherries and boxed cake mixes made pineapple upside-down cake one of the most popular desserts in America.
The cakes were standard at bake sales and church potlucks and festive occasions, with its heyday being throughout the 1950s and 1960s. Today, it’s considered a retro treat.
PINEAPPLE UPSIDE-DOWN CORNMEAL CAKE
An Alton Brown recipe
The addition of cornmeal makes this version a little more palatable to the modern tongue, because it makes a less sweet cake than you would get using a boxed mix.

Photo by Jennifer Reynolds
INGREDIENTS
¾ cup whole milk
1 cup stone ground cornmeal
1 stick unsalted butter
1 cup dark brown sugar
6 slices canned pineapple in syrup
6 maraschino cherries
1⁄3 cup chopped pecans
3 tablespoons syrup from pineapple can
3 whole eggs
1 cup all-purpose flour
2 teaspoons baking powder
½ teaspoon salt
¾ cup sugar
½ cup canola oil
DIRECTIONS
Preheat oven to 375 F.
Bring milk to a boil. Add the cornmeal. Stir and let soak 30 minutes.
Melt butter in 10-inch skillet over medium heat. Add brown sugar and let dissolve. Remove from heat and carefully place the pineapple slices in the skillet, one in the center and the rest circling it. Place cherries in the center of each pineapple. Sprinkle with nuts and drizzle with the syrup. Set aside.
Mix flour, baking powder and salt in a medium bowl. Mix eggs, sugar and whisk. Add oil and whisk. Add cornmeal to egg mixture and whisk. Add to flour and stir until combined. Pour batter over fruit.
Bake for 40-45 minutes. Cool for 30 minutes. Set platter over top of skillet, invert and serve.
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