Both simple and elegant, This jazz era cake has all the bells and whistles; from the taste: vanilla sweet, caramelly, and fruity, to the appearance: Golden pineapple rings, and bright red cherries, and a lusccious ooey-gooey syrup, to the catchy convention challenging name: it’s Upside Down! What’s not to love about this tasty treat? Informal when eaten plain or dressed up with a scoop of vanilla ice cream or some whipped cream for an elegant dessert. The recipe originated with desserts baked in Revolutionary War times when fruit was placed in a pan and covered in a simple batter, to be cooked over an open fire, or if available in a bread oven. Shortly after 1911 the Dole Company perfected the ring slicing and canning technique and started selling canned pineapple rings. The popular Maraschino Cherry from Croatia had been around since at least the 19th century. A whole pitted Marasca Cherry preserved in Maraschino liqueur, the rare and expensive treat was available almost exclusively to the very wealthy or royalty, and sparked the development of “Imitation Maraschino Cherries.” In 1920, Prohibition banned the import of the alcohol preserved genuine article, prompting the popularity of the non-alcoholic garnish that ironically nowadays appears almost exclusively in mixed drinks!
The graphic golden pineapple rings and jewel like red cherries fit the Art Deco style requirements of luxurious ingredients, glamorous appearance, and machine age modernity. One of the first recipes can be traced to a Gold Medal Flour ad from November of 1925. Modern food for a Modern Age.
I like to make this in an 11” x 11” x 2” square cast iron skillet. (My skillet is very old, so I don’t know if you can still get one in these dimensions) If you don’t have a square skillet, a 12” diameter round one will do fine.
To start, preheat the oven and the skillet to 350 degrees Fahrenheit.
Ingredients for Topping:
1/3 cup butter
3/4 cup firmly packed brown sugar
1 20oz can sliced pineapple (enough for 9 rings or more if you use a round pan) Drain and reserve the juice
1 jar of red stemless maraschino cherries
Ingredients for Cake:
2 cups all-purpose flour
1 tablespoon baking powder
1/4 teaspoon salt
1 cup firmly packed brown sugar
2/3 cup butter, softened
3 large eggs
2 teaspoons vanilla extract
3/4 cup milk
Directions:
Prepare the topping first.
Once the skillet is hot enough, carefully melt the 1/3 cup butter in the pan. Swirl it around to coat the bottom of the pan. Sprinkle the 3/4 cup brown sugar across the bottom of the pan. Evenly spread it with a spoon to make sure all the sugar is mixed with the butter. Once the sugar has mostly dissolved, arrange the pineapple slices across the top. Place a maraschino cherry in the center of each slice, and if desired in the diamond shaped openings between the rings.
Prepare the cake batter.
Combine the flour, baking powder and salt; set aside. Combine 1 cup brown sugar and 2/3 cup butter in bowl; beat at medium speed, until creamy. Continue beating and add the eggs one at a time, until well mixed. Stir in vanilla. Gradually beat in the flour mixture on low speed, alternating with the milk, scraping the bowl after each ingredient.
Spoon the batter over pineapple and spread evenly. Bake for 35-40 minutes or until a toothpick inserted in the center comes out clean. Loosen the sides of cake from the pan by running a knife around the inside of the pan. Invert the cake onto a serving platter and let stand for at least 5 minutes to allow the topping to “unstick” from the bottom of the pan. Remove the pan and let cool.
Slice and serve as is or with a scoop of vanilla ice cream.