While the term "upside down cake" was first used circa 1870, the cooking style dates all the way back to pies and tarts made during the Middle Ages. Modern cakes didn’t appear until the mid-19th century, but when recognizable upside down cakes did appear, they were first made with fruits like apples and cherries. Upside down cakes were popular because they were essentially self-decorating and could be made in a skillet, which was important as many people did not have ovens at the time, so they had to use recipes that could be cooked on a stovetop or over coals. Pineapples rose to popularity as a status symbol in the 16th and 17th century because they were incredibly expensive to procure and often cost thousands of dollars for a single specimen. Then in 1899, a Massachusetts businessman named James Drummond Dole moved to Hawaii to start a coffee business. After his venture proved unfeasible, he founded the Hawaiian Pineapple Company (which later became the Dole Food Company) in 1901. While Dole was not the first person to mass-produce or sell canned pineapple, he was very dedicated to marketing his product and his efforts helped revive national interest in the fruit. In 1925, the Hawaiian Pineapple Company ran a contest to collect recipes for a forthcoming cookbook called Pineapple as 100 Good Cooks Love It. The contest would be judged by a panel of food experts there was even a $50 cash prize. After running ads in a few women’s magazines, the company received over 60,000 submissions. The winner was a pineapple upside down cake recipe created by Mrs. Robert Davis of Norfolk, Virginia. Interestingly, 2,500 of the submissions were also for some version of pineapple upside down cake! While we do not know the exact origin of pineapple upside down cake, we can infer from the large amount of recipe submissions coupled with the rise of canned pineapple that it was created and gained popularity sometime during the early 1900s. We do know that the two earliest written records for the dessert come from a Seattle charity cookbook printed in 1924 and a Gold Medal Flour print ad from 1925. The Boston Globe also published a pineapple upside down cake recipe on December 21, 1925, but it's not known whether this came before or after the Hawaiian Pineapple Company’s recipe contest. After the successful contest, Dole ran a series of ads centered around how many people had sent in their recipes for pineapple upside down cake, which further cemented the dessert’s popularity in America. More recipes began popping up and the cake was also featured in several ads run for Crescent baking powder, Spry vegetable shortening, and the Pineapple Growers Association. Around 1969, Betty Crocker released a pineapple upside down cake recipe (which, of course, called for a can of Dole pineapple slices). As the cake’s popularity grew, its reputation shifted from something relatively utilitarian that could be made by people who didn’t have access to an oven to a trendy, more elegant dessert often served for special occasions. Today, pineapple upside down cake is considered a classic and is still served at potlucks, parties, and bake sales, especially in the Midwest. There is even a National Pineapple Upside Down Cake Day celebrated on April 20th of each year!