Perhaps the 20th century's most notorious, retro-chic dessert creation, Pineapple Upside-Down Cake flips the traditional notion of a baked good on its head, pairing a spongy, yellow cake bottom with a glistening spread of pineapple rings and maraschino cherries on top.
Tarte Tatin, Tansy, Cobbler, Bolo de Banana
Key Ingredient Spotlight: Pineapple
Staring in the early 1700s, pineapples were part of cargoes coming from the Caribbean to North America. Yet despite Captain James Cook helping the fruit to find a natural home in Hawaii in the 1750s, the fresh fruit was a rare and expensive commodity in the United States until after World War I.
While buying the canned version might be a time saver, slicing a pineapple is not quite as daunting as you might imagine and will significantly enhance the flavor of your dish. The ideal density for the pineapple rings is 3/4" thick, with all brown spots (known as "eyes") and the center core (which is only quasi-edible) removed.
Upside-down cakes are not just limited to pineapple, and have been made with a wide variety of fruit ingredients. The original upside-down cakes, often referred to as "skillet cakes" because they were baked in a cast iron skillet with the fruit caramelizing on the bottom then flipped onto a serving tray, were primarily made with cherries and apples in the late 1800s. Today, upside-down cake varieties can be seen with a host of ingredients, from plums to apricots.
Not a fan of maraschino cherries? The original options for studding the pineapple rings were pecans and walnuts.
The concept of an "upside down cake" has been a mainstay of European cuisine since the Middle Ages, when unleavened cakes were created with a pancake-like batter and dotted with apples or any number of dried fruits. Early settlers in the United States continued this tradition, baking "spider cakes" (called as such in reference to their cooking vessel, cast-iron skillet with legs) over open flames, often with a shortbread bottom.
The upside-down cake led a fairly unassuming life until James Dole and the Hawaiian Fruit Company (later rebranding to the founder's namesake) began canning and selling pineapple in 1903. The fruit quickly became a favorite ingredient for celebration desserts and party cakes of all varieties. While the first record of the "true" Pineapple Upside-Down Cake is hotly contested (candidates include a recipe in Gold Medal Four Magazine in 1925, a recipe in the U.S. Department of Agriculture's Aunt Sammy's Radio Recipes in 1931, and a cake for sale in a Sears Robuck catalog in 1936), its place as one of a few truly American dishes makes it a homey, comforting treat.
While there is much debate over the source of the first pineapple upside down cake, the widespread love for this retro dessert was fueled almost entirely by Dole. In 1925, Dole held a pineapple recipe contest in order to familiarize the American population with the arrival of their "exotic" new product, with the promise that the 100 winning recipes would be included in a pineapple-themed cookbook the following year. Dole received over 60,000 recipes—2,500 of which were for Pineapple Upside-Down Cake. The public's interest was clearly piqued, and Dole saw an opportunity to capitalize on the popularity of the cake. The company ran a major ad campaign in 1926 based on the overwhelming number of Pineapple Upside0Down Cakes submitted, securing the dessert's place as a national favorite.
April 21 is celebrated annually as National Pineapple Upside-Down Cake Day.
Want to make it at home? Get the recipe here: Pineapple Upside-Down Cake
All products linked here have been independently selected by our editors. We may earn a commission on purchases, as described in our affiliate policy.