I don't know what was more appealing to me as a kid - the juicy yellow pineapple ring, the bright red cherry that sat like a bullseye in the middle of the pineapple ring, or the sweet mushy brown stuff that surrounded them both - but I can tell you that to this day, pineapple upside down cake reminds me of my Uncle Lee. He's my father's brother and former Senior Chef at the elite New York Yacht Club for more than 20 years and gone way too soon.
Uncle Lee, who lovingly called me String Bean as I was super skinny as a kid, made sure the dessert table was covered with all kinds of sweet thangs. Everything, and I mean everything, was made from scratch - pumpkin pie, sweet potato pie, apple pie, lemon meringue pie, a variety of cakes and cookies, cobblers of every kind, and more, covered his dining room table and overflowed to a card table that sat off to the side. Ah, but the pineapple upside-down cake, tender and buttery, was my favorite. I'd wash down my hunk of a slice with a tall glass of something cold, but today, my equally generous slice is paired wonderfully with a hot steamy cup of dark roast coffee.
When I became an adult and left home to join the Air Force, my leave time always included a visit to Uncle Lee's house, and I was always his String Bean. Although Uncle Lee is no longer with us, my family continues the dessert table tradition at pretty much every occasion where sweet thangs have come to be expected; and you can bet that pineapple upside-down cake never loses its childhood appeal. Homemade desserts, along with memories of the best uncle ever, continue to fill me and satisfy me in ways my mouth full of sweet teeth could ever be.
Pineapple Upside Down Cake
Ingredients
Topping
- 1/4 cup butter, melted
- 1/2 cup brown sugar
- 20-ounce can of pineapple slices, drained (or fresh pineapple)
- Pitted maraschino cherries
Cake
- 1/2 cup butter, softened
- 3/4 cup sugar
- 2 eggs
- 1 teaspoon vanilla extract
- 1-1/2 cups all-purpose flour
- 1-1/2 teaspoon baking powder
- 1/4 teaspoon salt
- 1/2 cup milk
Instructions
Preheat oven to 350 degrees and grease an 8" x 8" baking dish.
Topping: Sprinkle the brown sugar on the bottom of the baking dish. Melt butter and pour over the top of the brown sugar, mix together, and spread evenly over the bottom of the dish. Place the pineapple rings on top of the brown sugar mixture, then place a cherry in the center of each pineapple slice.
Cake: Add the butter to a large mixing bowl and cream for 1 minute. Add the sugar and cream again for one minute. Add the eggs one at a time and mix thoroughly with each addition. Add the vanilla and mix. Combine flour, salt, and baking powder. Sift into the bowl and mix. Add the milk, mix and then gently spread cake batter over pineapple. Bake for 40 minutes or until golden brown and a toothpick comes out clean. Let cool to room temperature and turn cake upside down onto a cake plate.
If you use canned pineapple, an 8" x 8" pan works well to fit all the rings. If you choose to use a larger pan to fit more pineapple, just know that your cake will not be as thick.
Pineapple Upside Down Cake zoomed to popularity shortly after the invention of canned pineapple in the early 1900's. When the Hawaiian Pineapple Company (now Dole Pineapple) sponsored a recipe contest in the mid-1920's, fully 2,500 of the more than 60,000 recipes were for pineapple upside down cake.