When I was a boy, women, like my mother, seemed to await the arrival of each day’s newspaper just to see what new recipes were being featured. We never knew what might catch her eye in the recipe department. I remember one cake very well, and I still have her original clipping that she saved from the San Antonio Light – Pineapple Upside Down Cake. She seemed so pleased that she was able to invert her cake after baking and reveal the pineapple rings perfectly. Today it is suggested that it be baked in a cast-iron frying pan since the heavy steel keeps the butter from burning and its handle makes it easy to flip it upside down. It is very likely that all early cakes were baked this way since baking in an oven became feasible only around the 1920’s.

I didn’t find the recipe in the Fredericksburg Home Kitchen Cookbook, nor did I find it widely represented in my cookbook collection.  Possibly people thought it was a frivolous recipe or maybe it didn’t have a very wide following, but if that is the case, why have we all heard of it and probably eaten it at one time or another? Today, the concept of upside downness seems to have run its course. By the mid-60s this cake vanished all together, but the upside-down rage actually began in the late 1800s when cakes like this were referred to as skillet cakes. Inverting these cakes revealed toppings that were actually very popular as far back as the Middle Ages. 

Before pineapples, the fruits used were apples and cherries. About 1901, canned pineapples began appearing for the first time when Jim Dole established his Hawaiian Pineapple Company (Dole) and invented a machine to cut his pineapples into nice rings. Soon the convenient and pretty rings were used in the age-old technique of the skillet cake. In 1925 Dole even sponsored a contest calling for pineapple recipes. Nearly 5% of the 60,000 submissions were recipes for upside-down cakes. Recipes began appearing in magazines, cookbooks, and advertisements. By 1930 the cakes were first mentioned in print. For the next 30 years they proved popular, and one could say they had a good run.

So what was so special about the pineapple? The original home of pineapples was Brazil yet no primitive form of them has ever been found. How it evolved remains a mystery, but cultivation spread to the West Indies even before Columbus arrived. By the mid-1600s pineapples were being grown in India and shortly thereafter they reached China. It was Captain Cook who introduced them to the Pacific islands. In Europe they quickly gained acceptance and found their way into fine art. Canned pineapple first began to appear in Hawaii in 1892. 

A pineapple, just like a peach, does not continue to ripen nor sweeten after picking. A fully ripened pineapple can be identified by pulling out a leaf from its crown; it should come away easily. One can root its top and it will grow into a new pineapple, but one word of caution: pineapples contain bromelin, an enzyme which breaks down protein like a meat tenderizer. If working with pineapples a lot, rubber gloves to protect the hands are a must.

If you have a fond memory of eating Pineapple Upside Down Cake or have always heard of it and never tried it, I have two recipes for you below.

Here is my mom’s recipe from the San Antonio Light from years ago:


1/3 cup unsalted butter
2/3 cup packed brown sugar
1 20 oz can pineapple slices, drained, juice reserved
½ cup chopped pecans
3 large eggs, separated, room temperature
1 cup sugar
1 tsp vanilla extract
1 cup all-purpose flour
1 tsp baking powder
½ tsp salt
9 maraschino cherries


Preheat oven to 375ºF
In an ungreased 9-inch square baking pan, combine butter and brown sugar.
Drain pineapple, reserving 1/3 cup juice.
Arrange 9 pineapples slices in a single layer over sugar.
Sprinkle pecan over pineapple; set aside.
In a large bowl, beat egg yolks until thick and lemon-colored.
Gradually add sugar, beating well.
Blend in vanilla and reserved pineapple juice.
Combine flour, baking powder and salt.
Add to batter, beating well.
In a small bowl with clean beaters, beat egg whites on high speed until stiff peaks form
Fold into batter and spoon into cake pan.
Bake 30-35 minutes or until toothpick inserted in center comes out clean.
Let stand 10 minutes before inverting onto a serving plate.
Place a cherry in the center of each pineapple slice.

By Mark Wieser

Leave a Reply