The idea of cooking a cake upside down is an old technique that started in the middle ages when cakes were cooked in cast iron skillets. It was easy for the cook to add fruit and sugar in the bottom of the pan and a simple cake batter on top and put it over the fire to cook. Flipping it over onto a plate was a natural way to show the pretty fruit and to let the hot glaze run into the cake as well. The idea of using pineapple dates to soon after 1911 when James Dole of the Hawaiian Pineapple Company had both a machine to cut his pineapples into nice rings and the ability to can them as well. One of the earliest printed recipes for pineapple upside down cake is from a 1924 Seattle fundraising cookbook. The later invention of the maraschino cherry added the necessary color needed to make this cake visually appealing.