The recipe scanned from the Betty Crocker New Picture cookbook (1961). Click to enlarge.
Start by gathering your ingredients. Unless you've got helper monkeys and endless counter space (sadly, I have neither), do yourself a favor and make sure you have a clean, clear counter to work on and all of the ingredients at hand.
If using fresh pineapple (which I recommend), prepare it. If using canned, well, open the can, I guess ;) You can use rings, tidbits, crushed, whatever floats your boat... it just depends on what you want the end result to look like.
You can do this recipe in a baking dish such as a pyrex or ceramic dish, however I prefer a cast iron skillet. I find they heat/cook more evenly and it goes easily from stove to oven. In whatever dish you choose, melt the butter in the bottom.
Add the brown sugar and stir to combine, covering the bottom of the baking dish evenly. You can substitute (or combine) sweeteners here... honey, maple syrup, molasses, etc. Anything that will give you a liquid-y base will work.
Arrange your pineapple pieces in the brown sugar/butter syrup. I went for a mosaic/paving stone design. Try and keep the pineapple in a single layer to ensure the final cake will hold together properly when being unmolded.
In the bowl of a stand mixer (or with a hand mixer), add the wet ingredients (milk, vanilla and egg)...
And beat the living daylights out of them. Add the shortening and beat until well blended (no shortening lumps!). In a separate bowl or a sifter, mix dry ingredients (flour, sugar, baking powder, salt) and add to the wet. Beat for a bit longer until smooth and slightly fluffy.
Pour directly into baking dish and using a spatula, spread over pineapple pieces.
Make sure the cake batter is as even as possible to ensure even baking. Put into a 350F oven and set the timer. Check part way through baking to ensure all is well... it's ready when a cake tester comes out clean.
Using my cast iron skillet, the cake came just up to the top of the lip and the edges were a nice golden color. Total baking time for me was 45 minutes... this may vary depending on your oven and what dish you choose to bake in.
A word to the wise... make sure you have a plate large enough to flip the whole thing onto once it comes out of the oven. I didn't do this and once I had a hot cast iron skillet full of pineapple-y goodness, I realized it was slightly larger than the plate I'd intended to use! So, I had to flip it out onto a cookie sheet and then transfer it really carefully onto a plate, which was a pain in the patoot. At any rate, while still warm, flip the skillet/dish over and leave it like that for a few minutes. This will allow the cake to release itself from the bottom and settle slightly.
Then remove the dish and behold your beautiful cake! This is, of course, the classic way to serve this cake. If you prefer, you can leave it right side up and in the dish and simply serve it by scooping it out as you would a pudding cake.
After oohing and aahing and proclaiming it the prettiest cake you've ever made, serve it warm. Goes well with vanilla ice cream, a bit of whipped cream, or even just a light sprinkle of icing sugar. Can be stored in the fridge and reheated, but really is best fresh out of the oven. I imagine you could even do this recipe in individual-sized dishes, though I don't know how that would affect the baking time. So just to be on the safe side, recruit all the help you can to make sure it gets finished in one sitting ;) Enjoy!