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A Mad Men Recipe: Pineapple Upside Down Cake

Pineapple Upside Down Cake

My roommate and I decided to host a Mad Men Party and she made this delicious Pineapple Upside Down Cake. It is very easy and was a real hit at the party.


For the topping
5 tablespoons butter
3/4 cup brown sugar
8 slices canned pineapple slices
pecan halves, for decorating
maraschino cherries, for decorating

For the cake
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.

Recipe Credit: Mad Men Unofficial Cookbook

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