Aunt Lil’s Pineapple Upside Down Cake

Aunt Lil's recipe

Pineapple Upside-Down Cake screams retro cooking doesn’t it? I’m sure many of you grew up enjoying this cake baked by your mother or grandmother. But sometime late in the 20th century the cake fell out of fashion. This was too bad, as it’s a delightful and easy to make cake that also looks beautiful.

It’s not surprising that Aunt Lil had a recipe for Pineapple Upside-Down Cake in her cook book. What’s truly amazing though is that she wrote out the directions – one of the few recipes from her cook book where she did this. It certainly helped me to make the cake, though I still found a similar recipe to follow from Ruth Berolzheimer’s The United States Regional Cook Book, 1947.

Cakes or puddings baked in cast iron skillets with fruit on the bottom date back quite far into culinary history. But it wasn’t until the 20th century that pineapple became the fruit of choice. It was thanks to James Drummond Dole that pineapple became a fad staple. In 1903 he invented a process of slicing and canning the pineapple that allowed¬† for easy shipment.

No one knows who invented the cake, but by the 1920s recipes were everywhere in newspapers, ladies magazines, and cook books. A recipe contest held in 1925 by the Hawaiian Pineapple Company (later Dole) resulted in 2,500 versions of Pineapple Upside-Down cake. The winning recipe by  Mrs. Robert Davis of Norfolk, Va. was published in the cookbook of prize winners.

1952 Dole ad with pineapple upside-down cake recipe

To learn more about the history of this cake you might want to check out this blog. It’s certainly gives a very full history of this popular dessert.

Here’s Aunt Lil’s recipe. I encourage you to give it a try. It’s very good!

  • 1/4 c. butter
  • 1 c. brown sugar
  • 2 eggs, beaten
  • 3/4 c. white sugar
  • 1 c. flour
  • 2 tsp. baking powder
  • tiny pinch of baking soda (I used 1 tsp.)
  • tiny pinch of salt (I used 1/2 tsp.)
  • 1 can crushed pineapple

    Cake batter

Melt butter in a 9 or 10″ cast iron frying pan.

Add brown sugar, stir until melted

Drain pineapple and reserve 1/2 cup

Arrange pineapple in the pan

Sift flour, baking powder, baking soda and salt together

Beat eggs until light and fluffy

Beat the white sugar into the egg mixture gradually

Alternatively mix the flour and 1/2 c. pineapple juice into the egg mixture

Mix only enough to blend

Pour batter over fruit

Bake in a 350 degree oven for 50-60 minutes

Cool slightly

Invert onto serving plate

Makes 8-9 servings

Finished cake

I’d love to hear from you about your memories of Pineapple Upside-Down Cake. And do pull out your mom or grandmother’s recipe and give it a try again!


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