Pineapple upside down cake has always been a bit of a problem food for me. While I love the concept of cake studded with pineapple that’s been cooked in butter and brown sugar and soaked in the resulting sauce, the execution is almost always tooth-achingly treacly for me. Many versions use pineapples canned in syrup and then still load the whole thing down with sugar without even pretending to care how sweet it is. I’ve seen several recipes that don’t even try utilizing salt for balance (side note: you should be wary of baked goods that don’t employ salt.) I like mine made with fresh pineapple, as it has tartness that its canned counterpart lacks, and slightly less sugar than other versions. This still makes a sweet cake, but not so sweet that you can’t taste anything else. I also like to fancy-pants mine up by adding half a vanilla bean and its scrapings into the topping, but if you don’t have one on hand, it’s not going to break this cake.
For the pineapple topping*:
1 ripe pineapple, skin removed, quartered lengthwise, and core removed. (You’ll likely have some pineapple leftover for snacking.)
4 tbsp butter
1/2 cup light brown sugar
A healthy pinch of kosher salt
Scrapings and pod from 1/2 vanilla bean
For the cake:
1 stick butter
1/4 cup dark brown sugar
2 tbsp granulated sugar
1 teaspoon vanilla extract
1 cup all purpose flour
3/4 tsp baking soda
Heaping 1/4 tsp kosher salt
1. Preheat the oven to 375 degrees. Cut the pineapple into 1/2″ thick slices.
2. First, make the pineapple topping: In a 9-10″ cast iron skillet/oven safe skillet over medium low heat, heat the butter, brown sugar, vanilla bean and scrapings, and salt until melted and bubbling. Add the pineapple slices in a single layer covering the bottom of the pan and simmer for five minutes, then use tongs to flip the pineapple pieces to cook for a few more minutes on the opposite side. You want the fruit to be just tender when pierced, but not even approaching soft or mushy.
3. While the pineapple cooks, make the cake: In the bowl of a stand mixer fitted with the paddle attachment, cream the butter and sugars until light and fluffy (and really, I mean fluffy. Don’t just mix until combined.) Add the eggs, one at a time, mixing well after each addition. Add the vanilla extract, scrape down the bowl, and mix for a few seconds more.
4. Stir together the flour, baking soda, and salt, then add to the egg mixture in two batches, mixing as little as necessary to incorporate the flour.
5. Finally, assemble the upside down cake: Once the pineapples are done, remove from heat and spread the cake batter over the pineapples. Don’t worry if the batter doesn’t stretch all the way to the edges- it will spread a bit during baking. Place the skillet in the oven and cook for 15-20 minutes or until the cake is golden around the edges and springs back in the center when poked.
6. Let the cake cool for 15 minutes, then run a knife between the edge of the cake and the pan and flip onto a serving platter/plate. The easiest way to do this is to invert a plate over the cake in the pan, hold it tightly together, then flip it. Place it on the counter and lift the pan, letting the cake slide out onto the plate. Serve warm. This cake is best served soon after baking.
*For an even better version of this, add a bit of rum to the topping and flambe it before adding the cake batter to the pineapple topping. Do this, preferably, in front of people to show them how awesome your dessert-making skills really are.