Mad Men: Pineapple Upside Down Cake

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 the dish it inspired here) 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.

Mad Men: Pineapple Upside Down Cake
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  • 5 tablespoons butter
  • 3/4 cup brown sugar
  • 8 slices canned pineapple slices
  • pecan halves
  • maraschino cherries
  • 10 tablespoons butter
  • 1 1/2 cups granulated sugar
  • 2 large eggs
  • 2 cups all-purpose flour
  • 3 teaspoons baking powder
  • 1 teaspoon salt
  • 1/2 cup buttermilk
  • 1/4 cup syrup from pineapple can
  • 1 teaspoon vanilla extract
  1. Line a 10-inch cast-iron skillt with aluminum foil, completely covering the bottom and sides and extending extra foil over edges of pan. Preheat oven to 350F. 
  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.
  3. Arrange pineapple slices over butter/sugar spread. Place cherries in center of pineapple and pecans between the slices.
  4. 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.
  5. 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 evently across mixture in skillet.
  6. 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. 
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