Ingredients for the upside-down
- 4 Tbsp unsalted butter, plus more for the pan
- ⅓ cup (73 g) lightly packed dark brown sugar
- 1 ½ Tbsp black rum or pure vanilla extract
- Pinch of salt
- 1 20-oz can sliced pineapple, drained
- 10 Maraschino cherries
Ingredients for the cake
Makes one 10-inch round cake
- 1 ⅓ cup (180 g) unbleached all-purpose flour
- 1 ½ tsp baking powder
- 1 ½ tsp ground cinnamon
- ½ tsp kosher salt (or ¼ tsp fine sea salt)
- ¼ tsp ground cardamom
- 4 Tbsp unsalted butter, at room temperature
- 2 Tbsp neutral oil (vegetable, canola, or avocado work great)
- 1 ¼ cups (200 g) white granulated sugar
- 1 large egg, at room temperature
- 1 ½ Tbsp black rum or pure vanilla extract
- ½ cup buttermilk, at room temperature
A classic pineapple upside-down cake is just that, a classic. Everyone’s heard of it. At heart, it’s simple: a fluffy yellow cake topped with buttery brown-sugar, sliced pineapple, and maybe some maraschino cherries if you’re feeling flirty.
Almost any fruit can find its way into upside-down cake, but for now we’re sticking with the classic pineapple-cherry combo. Of course, I can’t leave well enough alone, so to celebrate the transition from summer to fall, we’re pairing summer-y pineapple with warming spices and adding a few splashes of dark rum for good measure.
The spices work so well with the sweet-tart pineapple, and the rum adds even more warm flavor. For spices, we’re sticking with cinnamon and a kiss of cardamom. We opted for dark rum because light or silver rum wouldn’t have enough punch to shine amidst the other flavors. But, honestly, the important detail here is the cake’s garnish: topping it off with a massive scoop of soft melty vanilla ice cream is absolutely essential.
By Billy Green
Position a rack in the center of the oven and heat the oven to 350ºF. Lightly grease a 10x2-inch round cake pan with a bit of softened butter.
Drain the pineapple. Lay the slices on a rimmed baking sheet lined with several layers of paper towels. Holding a few layers of paper towels in your hands, press down on the pineapple slices to soak up excess juice. If there’s too much liquid from the pineapple, the cake might be soggy.
Make the upside-down topping. In a small saucepan over medium heat, melt the butter. Gently whisk in the brown sugar, rum, and salt (if you’re cooking over an open flame, add the rum off the heat). Whisk the mixture constantly until it starts to bubble and then pour into the prepared cake pan. Carefully tilt the pan to evenly coat the bottom. Set the pan aside and let it cool for 5 minutes.
Arrange the pineapple rings around the edge of the pan, overlapping the slices slightly. After you’ve placed about 9 rings around the edge, tuck the last ring under the first. Place one more ring into the center of the pan. Place one maraschino cherry in the center of each ring. Set aside the pan while you make the cake batter.
Make the cake batter. In a small mixing bowl, whisk together the flour, baking powder, cinnamon, salt, and cardamom. Set aside. In the bowl of a stand mixer fitted with the paddle attachment, beat together the butter and sugar at medium speed until the mixture becomes light and fluffy, about 3 to 4 minutes. With the mixer running, add the oil and beat until it’s blended in. Turn off the mixer. With a rubber spatula, scrape down the sides of the bowl. Crack the egg into the bowl. Add the rum. Beat on medium-low to thoroughly incorporate, about 30 seconds. Turn off the mixer and scrape down the sides of the bowl. With the mixer running on the lowest speed, add half of the flour mixture to the bowl and mix just until combined. Pour in the buttermilk and mix until combined. Mix in the remaining flour just until combined. Turn off the mixer, scrape down the bowl, and then mix very briefly on medium speed just to ensure all of the ingredients are combined.
Bake the cake. With a large mixing spoon, carefully scoop batter into the prepared cake pan. Try to make an evenly thick layer of batter over the pineapple. Use a rubber spatula to gently smooth out the batter in the pan. Try to not disturb the pineapple-slice arrangement in the bottom of the pan. Place the cake pan on a baking sheet just in case there’s a boil over from the caramel, and bake in the preheated oven until the top is a nice golden brown and a toothpick inserted into the center of the cake comes out clean, 40 to 45 minutes.
Let the cake sit in its pan on a cooling rack for 5 minutes (no more or the cake could stick!). Then carefully run a knife around the edge of the pan to help the cake easily release from the pan. Place a pretty serving plate over the top of the cake pan. The plate must be at least a couple of inches larger than the pan. Using two dry folded dish towels to protect your hands from the hot pan, hold the pan and plate firmly together and quickly flip the pan over. The cake should release easily, but tap the bottom of the pan a few times to ensure this. Then carefully lift the pan off the cake. If any bits of caramel or fruit stuck to the pan or moved around, just carefully nudge everything back into place on top of the cake (it’ll be our little secret). Serve the cake warm or at room temperature, sliced into wedges and topped with big scoops of vanilla ice cream.