George Washington wrote that of all fruits, “none pleases my taste as do’s the pine.” He had acquired a taste for pineapple in Barbados, and later bought it whenever possible, asking sea captains who traded his goods to bring pineapples back from the West Indies. But he was one of the lucky few to enjoy this fruit. It was so costly at the time, some hostesses would actually rent the fruit from bakers to display as a centerpiece, then return it uneaten. The pineapple would be rented out again and again, sometimes until it rotted!
There were occasional recipes for pineapple in 18th- and 19th-century British and American cookbooks. But most were just instructions for cutting and serving the fruit raw, or preserving it. As the 19th century progressed, pineapples were imported in larger numbers from Florida, the Caribbean, and Central America, and recipes for using them increased. Most of these were for preserves, compotes, and cold dishes like pineapple salad, ice cream, and Bavarian cream.
None of these cold desserts really appealed to me, however, and neither did the few recipes I saw for pineapple pudding and pie. What I really wanted was pineapple cake — I had fond memories of a pineapple upside-down cake that a great aunt used to make. I thought I might find its progenitor in 19th-century American cookbooks. But I learned there were almost no pineapple cakes back then, and nothing like the pineapple upside-down cake. It turns out that this cake wasn’t made, so far as we know, until the 1920s.
But the concept of upside-down cake is nothing new. As early as the Middle Ages, Europeans made some cakes by topping batter with fruit — usually apples or dried fruit — and cooking it over a fire (or baking it), then flipping it over for serving. In America, these were called “skillet cakes.” A similar French dish was the apple tarte Tatin, created in the 1880s. According to Gil Marks, who wrote about pineapple cake for Tori Avey, the first-known use of the term “upside-down cake” was in 1923, for a cake made with dried plums. The name was probably derived from “upside-down pies,” which appeared in the previous decade.
A few pineapple upside-down cake recipes were published in small regional cookbooks around this time. Pineapple consumption was on the rise thanks to cheaper prices and increased imports. The biggest reason for this change was James Drummond Dole’s cannery business in Hawaii, which started in 1901. Pineapple had been grown in Hawaii since the early 1800s, and there were canneries there by the 1880s, but none were on the scale of the Dole operation. Dole had a machine that could peel, core, and cut 100 pineapples per minute. Soon he and other Hawaiian growers were producing so much pineapple that they needed an advertising campaign to convince Americans to buy it all. Here is an ad from 1915, suggesting that canned pineapple was actually better than fresh:
Then in 1925, the Dole company sponsored a recipe contest for the best dish using pineapple, and ran ads for it in women’s magazines. The winner was a pineapple upside-down cake from Mrs. Robert Davis of Norfolk, Virginia. Dole received more than 2,500 submissions for pineapple upside-down cake (out of 60,000 recipes total), so clearly some people were making a version of this cake prior to 1925.
In any case, the Dole company promoted Mrs. Davis’s winning recipe widely, and soon pineapple upside-down cake was one of the most popular cakes in North America. I found the original winning recipe online and baked it recently, and my family devoured it. It was, after all, judged the best of 2,500 pineapple upside-down cakes! It has a light, fluffy crumb, and nicely caramelized fruit. And it’s very easy.
You can use fresh pineapple instead of canned, and I’m sure it will taste even better, but ironically, it won’t be as authentic. You can also use drained crushed pineapple, as mentioned in the original recipe, but I don’t think it will look as nice.
Maraschino cherries had become wildly popular in the United States in the early 1900s, which could explain why they were chosen as a garnish for this cake. Artificially dyed cherries were likely used on the 1920s cakes, but I opted for dye-free cherries, which are still bright and festive. Also, the original recipe suggests spreading whipped cream over the top of the cake if desired, but I think that would ruin the cake’s pretty top. Plus it’s superfluous — this cake is rich and delectable on its own.
Pineapple Upside-Down Cake
Adapted from the winner of the Hawaiian Pineapple Company Recipe Contest, 1925
2 cups all-purpose flour
2 teaspoons baking powder, non-aluminum preferred
½ teaspoon salt
2 eggs, separated, room temperature
½ cup unsalted butter, room temperature
1 cup granulated sugar
½ cup whole milk, room temperature
1 teaspoon vanilla extract
2 tablespoons unsalted butter
1 cup dark brown sugar
20-ounce can pineapple rings, drained, or about 8 slices fresh pineapple
approximately 1 dozen maraschino cherries
1. Preheat the oven to 350°F. Lightly grease a 9-inch cast-iron skillet. (You can also use a 9″ X 9″ X 2″ baking pan, but in Step 4, melt the butter before placing in pan.) Sift together the flour, baking powder, and salt, and whisk well.
2. Beat the egg yolks briefly, then beat the egg whites separately, until very frothy.
3. Cream 1/2 cup butter, then gradually add the white sugar, beating for about two minutes. Add the yolks to the creamed mixture and mix well. Then add the milk alternately with the flour, in about three installments, mixing well after each addition. Last, fold the beaten whites and vanilla into the mixture. Set aside.
4. Melt the remaining two tablespoons butter in the skillet. Spread the brown sugar evenly over the butter. Place pineapple rings on top, as close together as possible (you’ll have a few slices left over). Pour the cake batter over the fruit, distributing evenly.
8. Bake for 45 minutes, or until a toothpick inserted in the center of cake comes out clean. Immediately after removing from oven, run a knife around the edge of the cake, then carefully turn cake upside-down on a serving dish. Garnish with maraschino cherries. Serve warm or at room temperature. This cake is best the day it is made.