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KITTY’S PINEAPPLE UPSIDE-DOWN CAKE

SEASON 2, EPISODE 1

“For Those Who Think Young”

As Don and Betty Draper celebrate Valentine’s Day 1962 at New York’s Savoy-Plaza Hotel, ordering room service and watching Jackie Kennedy’s televised White House tour (see Jackie Kennedy’s Avocado and Crabmeat Mimosa), Salvatore Romano and his wife Kitty are watching the same program in their New York apartment. The dessert Sal and Kitty are enjoying in front of the TV is an American classic: pineapple upside-down cake, so-named because the fruit, sugar, and butter are put in the pan or skillet first, the batter poured over them, and the cake flipped over on a plate for serving.

Upside down cakes date to the late 1800s when cooks used skillets to make cakes because ovens were not yet reliable. But the pineapple upside-down cake first appeared in the 1920s when Jim Dole, founder of the Hawaiian Pineapple Company (later the Dole Food Co.), started canning up to 95 percent of his crop. This practice brought the once exotic fruit into the mainstream. When Dole Food Co. held a cooking with pineapple contest in 1926, more than 2,500 of the submissions were for pineapple upside-down cake.

Just as new foods inspired new recipes, new kitchen appliances inspired new ways to make them and cookbooks reflected the trend. “Cooking in an electric skillet or frypan (the words are synonymous here) is cooking at its best,” wrote Roberta Ames in The Complete Electric Skillet-Frypan Cookbook (1960), one of many period cookbooks designed entirely around a new kitchen technology. “I can think of no appliance which fulfills so many different functions…Recently I remarked to friend that if I had to choose just one household appliance, it would be the electric skillet.” Alas, the electric skillet is virtually extinct today, its utility diminished by more versatile electric ovens and stovetops.

New culinary tools also made their way into advertisements and cookbooks. “Make this Pineapple Upside-Down Cake with your Favorite Cake Mix…and turn it out perfect in Reynolds Wrap, The Pure Aluminum Foil!” declared a Reynolds print ad from the 1950s. Roberta Ames gave a nod to Reynolds Wrap (or perhaps it was an early example of product placement) in her pineapple upside-down cake recipe when she wrote, “The Reynolds Home Economic Staff suggested the use of foil in upside-down cake. This method does beautifully, and the cake is easier to remove than if baked right in the pan.” It does indeed work beautifully, and this adaptation of Ames’ pineapple upside-down cake includes this helpful tip. From the looks of Kitty’s version, she kept Reynolds Wrap on hand, too.

Pineapple Upside-Down Cake

ADAPTED FROM THE COMPLETE ELECTRIC SKILLET-FRYPAN COOKBOOK BY ROBERTA AMES (HEARTHSIDE PRESS, 1960)

NOTE: We have adapted this recipe for a cast-iron skillet.

For the topping

5 tablespoons butter

34 cup brown sugar

7–8 canned pineapple slices (reserve syrup)

Pecan halves, for decorating

Maraschino cherries, for decorating

For the cake

10 tablespoons butter

112 cups granulated sugar

2 large eggs

2 cups all-purpose flour

3 teaspoons baking powder

1 teaspoon salt

12 cup buttermilk

14 cup syrup from pineapple can

1 teaspoon vanilla extract

  1. Line a 10-inch cast-iron skillet with aluminum foil, completely covering the bottom and sides and extending extra foil over edges of the pan. Preheat oven to 350°F.
  2. Make the topping: Place butter in skillet, place skillet in oven, and melt butter. As soon as butter is melted, remove and stir in brown sugar, carefully mixing well with a rubber spatula so as not to tear foil. Arrange pineapple slices over butter/sugar spread. Place cherries in center of pineapple and pecans between the slices.
  3. Make the batter: In the bowl of an electric mixer, cream butter, adding sugar gradually, and then add eggs and beat well. Stir flour, baking powder, and salt together in a small bowl. Combine buttermilk, syrup, and vanilla in a small measuring cup. Add flour mixture alternately with buttermilk/syrup mixture, beating well after each addition. Spread batter evenly across mixture in skillet.
  4. Bake for approximately 45–50 minutes, or until toothpick inserted in center of cake comes out clean. Place a large cake plate over pan, and invert to remove. Peel off aluminum foil, pressing back any pineapple that may be stuck to the foil.

YIELD: 10–12 SERVINGS