Pineapple upside-down cake is one of the more toothsome desserts. I’ve discovered, however, that you can significantly improve the richness and texture of this cake by using a high-quality buttermilk cake and by using fresh pineapple.

Pineapple-Cherry Filling in Bottom of the Cake Pan

My version of the cake is arguably less attractive than more traditional versions for two reasons: I use crushed pineapple rather than pineapple rings; and I use dark- rather than light-brown sugar. My tendency is always to favor flavor over presentation. You get a much more distinctive pineapple flavor in this way. If you are more concerned about appearance, feel free to substitute pineapple rings and light-brown sugar.

This recipe makes two cakes. If you don’t need two, freeze one cake, which is what I always do. When the cake is cooled, place it in the freezer uncovered on a sheet of aluminum foil until it begins to harden. When firm, wrap it in the foil and place in a plastic bag to prevent that dreadful freezer taste. Thawed, your cake will taste as good as fresh made.

The Unmolded Cake

If you wish to simplify the recipe, by all means use two 20-ounce cans of sweetened fresh pineapple or a sufficient number of pineapple rings. I find the result is never quite as good, however.

To print or download the recipe, click here.