Preheat oven to 350 degrees. Line a 10-inch cast iron skillet with tin foil.
Place the 5 tablespoons of butter in the skillet and place in the oven to completely melt the butter. It will take about 5 minutes.
Once the butter is melted, add in the brown sugar. Stir the brown sugar and butter together carefully using a rubber spatula. You don't want to tear the tin foil at all.
Spread the brown sugar mixture evenly across the bottom of the pan.
Place the pineapple slices side-by-side in the bottom of the pan. Place a maraschino cherry in the center of each pineapple ring. Between each pineapple ring, add a pecan half.
In a large mixing bowl, add in the butter and granulated sugar. Mix on medium until combined. The mixture will be crumbly, not light and fluffy.
Add in the eggs one at a time. Mix each egg thoroughly before adding the next. Scrape down the sides.
In a separate bowl, sift together the flour, baking powder and salt.
In a liquid measuring cup, add in the buttermilk. If you don't have buttermilk, use milk and vinegar. I used heavy cream and cider vinegar. Let the milk and vinegar mixture sit for about 10 minutes.
Add the pineapple syrup into the buttermilk.
Alternately add the flour and buttermilk, starting and ending with flour. Mix each addition thoroughly before adding the next addition. The batter will be thick.
Spread the batter evenly on top of the pineapple topping.
Place in the oven for 50 minutes to 1 hour or until done. Place a toothpick in the center of the cake and if it comes out with moist crumbs, it's done. If there's still batter on the toothpick, let it bake a little longer.
Remove from the oven. Turn the cake out onto a cake plate. Carefully remove the tin foil from the sides of the cake. Cut and serve!
This recipe was from The Unofficial Mad Men Cookbook.
Pineapple Upside Down Skillet Cake https://www.cookiedoughandovenmitt.com/pineapple-upside-down-skillet-cake/