The pineapple upside-down cake went viral long before social media. The concept first appeared in the 1920s as an elegant, sophisticated dessert that took home the gold medal in a now-famous Dole recipe contest and after that the recipe was passed from housewife to housewife. Even to this day, its popularity hasn't waned. Now considered a retro classic, it still makes appearances at potlucks, picnics and barbecues and its trendiness is easily explained: It's super delicious, easy to make and truly a work of art.
Classic versions of this dessert features pineapple rings and maraschino cherries that are arranged in the bottom of a cake pan with butter and sugar, then topped with batter and placed in the oven. Once the cake is baked, it's inverted to reveal the gem-like fruit. And while the pineapple version made the upside-down cake widely known in North America, the concept was around long before then. Upside-down cakes used to be known as skillet cakes, which pre-date the modern oven, going all the way back to the Middle Ages. They were made in — you guessed it — a skillet over a fire or stovetop in which you'd first caramelize the fruit and sugar, then cover it with a batter. Once cooked, it was flipped to expose the beautiful self-saucing cake. For centuries, chefs and home cooks alike have experimented with different fruit and cake combinations to create a world of endless upside-down cake possibilities.
