The Kitchen Project says that cooks started baking cakes upside down because it was easy for them to add embellishments (be it fruit, sugar, etc.) to the bottom of the pan and then pour the batter over. Typically, they would cook the cake over an open flame and then flip it over for presentation. That way the toppings stayed intact and provided a nice look for the cake.
Though this method may not be as common today for cooks, the pineapple upside down cake remains prevalent as ever. If you're looking for a simpler version of it, perhaps with individual cakes, then Caitlin Cooks has you covered. Her recipe calls for common ingredients such as butter, milk, sugar, and of course, pineapples.
To start, create the sugar mixture and pour it into the bottom of your muffin tin. Then add your pineapples and maraschino cherries and top with batter. Throw the tin in the oven and once it's out, let the cakes cool before you indulge.
A full recipe for these mini pineapple upside down cakes is featured below.