Cast Iron Skillet Pineapple Upside Down Cake

This is my new favorite cake. Have I mentioned how much I love fruit? Well, in case you forgot, I really can't get enough of delicious fresh fruit. And this cake really has it all: fresh fruit, deliciously moist cake, buttery caramel sauce, and rum. Like I said, new favorite cake.

And this recipe is surprisingly easy, for how complicated it looks. It's as simple as heating the butter, brown sugar and rum in a cast iron skillet until bubbly, layering the pineapple in the caramel, then dumping the batter over top of the pineapple and sticking it in the oven for 30 minutes.

Inverting the cake wasn't really even that difficult, though the idea flipping a cake out of a hot cast iron skillet was a little intimidating! I'm really happy with how this cake turned out, and I'll probably make another one within the next couple days to share with more friends than I got too this time and also since I have a crap load of pineapple to use up. It was also a huge hit with the friends which I got to share this with, so I'm going to always keep this cake in mind when baking for gatherings.
I really encourage you to try making this cake, it's easy, it's delicious, and it looks like it was horribly tricky to make, which apparently impresses non-bakers ;), so it's really an all around win-win situation for everybody involved! Enjoy!!

Cast Iron Skillet Pineapple Upside Down Cake (adapted from Bijouxs)
Serves 6-8

1/3 cup (5 tablespoons) unsalted butter
3/4 cup dark brown sugar, packed
2 tsps rum of your choosing (I used Blackheart Spiced Rum)
7-8 slices of fresh pineapple, cut into 1/8" wedge slices
Maraschino cherries as desired
1/4 cup vegetable shortening
1/2 cup granulated sugar
1 1/2 teaspoons vanilla
1 large egg
1 cup all-purpose flour
1 1/2 teaspoons baking powder
2/3 cup milk
1/4 teaspoon kosher salt

Preheat the oven to 350°. Melt the butter in a 10-inch cast-iron or heavy ovenproof skillet. Add the brown sugar and rum and cook over a medium-low heat, stirring until the mixture is smooth and the sugar is completely dissolved, thick and bubbling. Remove from the heat and arrange the pineapple slices  in a concentric circle patter until the pan is covered. Place maraschino cherries as desired.

In a large mixing bowl or work bowl of a stand mixer fitted with the paddle attachment, beat the shortening and sugar until well mixed. Add the vanilla and the egg and beat well until the mixture is creamy and well blended. Combine the flour, baking powder and salt and add to the shortening mixture, combining well. Add the milk and mix until the batter is creamy and smooth.

Spread the batter evenly over the pineapple topping, gently spread to edges without disturbing the pineapple slices. Place the skillet on a baking sheet and bake in a 350° oven about 30 minutes, or until the top of the cake is golden brown.

Remove the cake from the oven and cool for 10 –15 minutes. Cover the skillet with a large plate and carefully invert the cake on to the plate, keeping the plate and skillet tightly pressed together as you invert the cake. Replace any pineapple slices that may stick to the pan onto the top of the cake. Serve warm or room temperature with freshly whipped cream, if desired.