Cast iron skillet pineapple upside down cake. This is the original, old fashioned pineapple upside down cake - I make mine in my grandmother's cast iron skillet, but you can use a regular cake pan if you don't have one. This homey, comfy dessert is a Southern classic - for good reason! Warm, caramelized brown sugar, bright pineapple, and rich buttery cake - everything good you're craving! Check out this video to see just how easy it is!