The Pineapple Upside Down Cakes

by | May 31, 2012 | Dessert, Recipes

Our father, Wayne Calhoun

Our father’s 85th birthday is today. It will probably be his saddest birthday as our mother, his wife of nearly 62 years, died a couple of weeks ago on Mother’s Day. Tonight my daughters, my sister Susie, and I will take him out for dinner. Last Sunday we did have a small gathering of his close friends and some family members to acknowledge his 85 year milestone.

Our mom and dad on a date in Santa Cruz

Pineapple upside down cake is our dad’s favorite cake, so on Sunday I set out to make a good one for him. I actually ended up making two pineapple upside down cakes. One of the recipes that I used was advertised as Dole’s original recipe. The other was an interesting recipe with fresh pineapple that I found on and tweaked a bit.

When I served the cakes everyone wanted to try a small piece of both. Hands down the cake with the fresh pineapple was the best.  It was much more moist and full of flavor. I’ve provided both recipes below.

The pineapple upside down cake with fresh pineapple and rum was the favorite

Fresh Pineapple Upside Down Cake


  • 1 medium pineapple, peeled, quartered lengthwise, and cored
  • 1 stick butter
  • 1 cup packed brown sugar


  • 1 1/2 cups all-purpose flour
  • 1/2 teaspoon ground cardamom
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 3/4 stick unsalted butter, softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla
  • 1 tablespoon dark rum
  • 1/2 cup unsweetened pineapple juice
  • 1 tablespoon dark rum for sprinkling over cake
  • Equipment Needed
  • 10-inch cast-iron skillet 


Preheat oven to 350°F.  Grease the skillet well. Cut pineapple crosswise into pieces about 1/2 inch thick. Arrange pineapple in the skillet in concentric circles, overlapping pieces slightly. Melt butter in a sauce pan. Add brown sugar and simmer over moderate heat, stirring, 4 minutes. Remove from heat and pour over the arranged pineapple.

Sift together flour, cardamom, 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 the batter over pineapple topping and spread evenly. Bake cake in the middle of the oven until golden and a tester comes out clean, about 45 minutes. Let cake stand in skillet 5 minutes. Invert a plate over the skillet and invert cake onto plate (keeping plate and skillet firmly pressed together). Some of the pineapple may have stuck to the bottom of skillet. Replace and rearrange any pineapple stuck to bottom of skillet and scoop up the brown sugar topping and fill in where needed. Sprinkle the rum over cake and cool on plate on a rack.

Serve cake just warm or at room temperature.

The pineapple upside down cake made from Dole’s original recipe

The Original Dole Pineapple Upside Down Cake Recipe


  • 1 20-ounce can either crushed -or- sliced Hawaiian pineapple
  • 2 cups flour
  • 2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/2 cup butter
  • 1 cup sugar
  • 2 eggs
  • 1 teaspoon vanilla
  • 1/2 cup milk
  • 2 tablespoons butter
  • 1 cup brown sugar
  • Maraschino cherries for garnish (I did not use these)


Drain the juice from 1 large can either crushed or sliced Hawaiian Pineapple. Sift 2 cups flour. Sift again with 2 teaspoons baking powder and 1/2 teaspoon salt. Cream 1/2 cup butter or substitute and gradually add 1 cup sugar; cream well. Beat yolks and whites of 2 eggs separately. Add yolks to creamed mixture; mix well then add flour and 1/2 cup milk alternately mixing well. Fold the 2 beaten egg whites and 1 teaspoon vanilla. Melt 2 tablespoons butter in a large oven-proof frying pan. Spread 1 cup of brown sugar over pan. Add pineapple (if sliced is used place slices closely together on the sugar; if crushed simply pour in the well-drained fruit). Pour cake batter over fruit. Bake 45 minutes. Turn upside-down on serving dish and garnish with maraschino cherries. Whipped cream may be spread over top.

Happy 85th birthday Dad!