Rum Butter Pineapple Upside Down Cake

Upside down cakes started as a thing of convenience, when cakes were often cooked in skillets. In the early 1900s, Dole’s pineapple rings hit stores, and by 1920 recipes for pineapple upside down cakes began to appear. Sometimes referred to as skillet cakes, this version calls for macadamia nuts and rum in addition to the traditional topping combination of brown sugar, pineapple, and cherries.

serving: 8
Prep Time: 45 Min
Chill Time: 8 Hr 0 Min

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  • 1/2 medium pineapple (about 6 rings) fresh or from the can
  • 3/4 stick butter
  • 1/2 cup spiced rum
  • 1 cup light brown sugar, firmly packed
  • 1/2 cup chopped macadamia nuts
  • 8 maraschino cherry halves


  • 1 1/2 cups all-purpose flour, spooned and leveled, plus more for pan
  • 2 tsp baking powder
  • 1/4 tsp salt
  • 3/4 stick unsalted butter, softened
  • 1 cup granulated suagr
  • 2 large eggs
  • 1 tsp vanilla (you can use vanilla bean paste)
  • 1 tbsp dark rum
  • 1/2 cup unsweetened pineapple juice
  • 2 tbsp dark rum for sprinkling over cake (optional)


Special equipment needed:
10-inch cast iron skillet

To make the topping, cut fresh or canned pineapple crosswise into 3/8-inch-thick pieces. Marinate pineapple in rum overnight.
Preheat oven to 350 degrees. Melt butter in cast-iron pan. Add brown sugar and simmer over moderate heat, stirring, 4 minutes. Remove from heat. Arrange pineapple on bottom of pan over the sugar mixture in a single layer; circles may overlap slightly. Place one cherry half inside each pineapple ring. You can add the nuts now or sprinkle toasted ones over the finished cake.

To make the batter, sift together flour, baking powder, and salt. Beat butter in a large bowl with an electric mixer until light and fluffy, then gradually beat in granulated sugar. Add eggs, 1 at a time, beating well after each addition. Beat in vanilla and rum. Add half of flour mixture and beat on low speed just until blended. Beat in pineapple juice, then add remaining flour mixture, beating just until blended. (Batter may appear slightly curdled.)

Spoon batter over pineapple topping and spread evenly. Bake cake in middle of oven until golden and a fork inserted in the middle comes out clean, about 45 minutes. Let cake stand in skillet 5 minutes. Invert a plate over skillet and invert cake onto plate (keeping plate and skillet firmly pressed together). Replace any pineapple stuck to bottom of skillet. Sprinkle rum over cake and let cool. Serve cake just warm or at room temperature.

Additional Tips

Cake can be made one day ahead and chilled, covered. Bring to room temperature before serving

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