Home-Cooked: Conrad’s Pineapple Upside-Down Cake


My father (affectionately nicknamed “Conrad”- a story for another time), has always been my immediate and extended family’s resident “cake-man.” Family reunions, birthday parties and other gregarious occasions were not complete without one of his sweet and delectable desserts. While growing up my childhood home was constantly filled with smells of warm vanilla, peanut butter icing or dripping wet cake batter. For a small period of time it made me sick to my stomach.  Now, as an adult, those same aromas bring a sense of nostalgia and comfort to mind.

One of my father’s most highly requested creations has always been his “Pineapple Upside Down Cake” and fortunately for me, his oldest child and only son, he’s agreed to loosen his grip on the recipe so I could try my hand at baking it. I should note, he’s a firm believer no one will EVER be able bake it quite like him, but I think I gave him a run for his money.

The recipe can be found below.

Recipe: Conrad’s Pineapple Upside Down Cake

Prep Time: 15 Minutes | Bake Time: 45 Minutes | Total Time: 60 minutes


For the topping:

1/4 cup Butter or Margarine

1 cup Packed Brown Sugar

2 cans Sliced Pineapples

1 can  Sweet Dark Cherries

For the Cake:

1 cup sugar

1 egg

1/3 cup Shortening (Butter Flavor)

1 1/4 cup of Flour

1 1/2 teaspoon Baking Powder 

1/2 teaspoon Salt 

3/4 cup Milk

1 teaspoon Vanilla Extract

1 teaspoon Lemon Juice


  1. Heat oven to 350 Degrees. In a 13×9 inch pan, melt the butter in the over. Once melted, sprinkle brown sugar evenly over the butter.

  2. Place pineapple slices on top of the brown sugar. In the center of each pineapple slice place a cherry.
  3. Place pan to the side.
  4. In a large bowl, cream  the sugar, shortening and egg together until it’s light and fluffy.
  5. Gradually fold in flour, salt, baking powder,  milk, vanilla and lemon juice until well blended. (Tip: To add a little flavor consider adding a teaspoon of pineapple juice from the can of sliced pineapples as well.)
  6. Pour cake batter over the pineapples, cherries and brown-sugar in the 13X9 inch pan.
  7. Bake for 45 minutes at 350 degrees or until toothpick inserted in the middle of the cake comes out clean.
  8. Once removed from the oven, run a kitchen knife around the edge of the cake to loosen. 
  9. Once loose, turn cake upside down on a heatproof plate. Let sit for 5 minutes with pan on top to allow the brown sugar to drizzle over cake. 
  10. Lift pan off the cake and let cook for 30 minutes before serving.

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