20 min
45 min
10
Cake
Makes one 10-inch cake
Some recipes don't need to be fixed. They just need better ingredients.
Pineapple upside-down cake has been around long enough to earn its reputation. Brown sugar melts into the bottom of the pan, fresh pineapple soaks up a little rum, and the whole thing flips onto a plate looking like you planned it that way. It's a good cake. It's always been a good cake.
The cherries, though — that's where most versions fall short. The bright red ones from the jar. You know the ones. They look the part, but they don't really taste like much.
That's where our new Cocktail Cherries come in. Made in Oregon, these are the real thing: deeply flavored, a little boozy, with a richness that holds up to heat and plays well with pineapple and caramel. Nestle them into the rings of pineapple before the batter goes in, and when the cake flips, each cherry is right where it should be — jewel-bright and worth eating.
Alison Roman's version of this cake uses dark brown sugar, a hit of rum, and a batter that gets beaten until it's nearly doubled in volume. It's more work than a box mix. It's also a better cake.
Make it for a crowd. Make it for a Tuesday. Either way, don't skip the good cherries.
Ingredients
For the Topping (which is actually the bottom):
- Cooking spray or softened butter, for the pan
- ½ cup dark brown sugar
- About ½ a pineapple, peeled, cored, and sliced about ½ inch thick
- 6-10 Oregon Fruit Cocktail Cherries
- 2 tablespoons dark rum or brandy (optional)
For the Batter:
- 2 cups all-purpose flour
- 1½ teaspoons baking powder
- 1 teaspoon kosher salt
- ¾ teaspoon baking soda
- ¾ cup buttermilk
- ½ cup vegetable oil
- 1 tablespoon dark rum or brandy (optional)
- 1 teaspoon vanilla extract
- 6 tablespoons unsalted butter, cut into 1-inch pieces, at room temperature
- ¾ cup granulated sugar
- ½ cup packed dark brown sugar
- 3 large eggs
- 2 large egg yolks
Directions
Step 1
Make the topping: Preheat the oven to 350°F. Spray a 10-inch cake pan with cooking spray or grease with butter. Sprinkle the brown sugar on the bottom of the cake pan.
Step 2
Mosaic the pineapple on the bottom of the cake pan, cutting pieces to fit the edges as needed. Decorate how you please with your cherries (in and around the rings of the pineapple). Drizzle rum over the pineapple, if using.
Step 3
Make the batter: In a large bowl, whisk the flour, baking powder, salt, and baking soda together. In a medium bowl or a measuring cup, combine the buttermilk, vegetable oil, rum (if using), and the vanilla.
Step 4
Make the batter: In a large bowl, whisk the flour, baking powder, salt, and baking soda together. In a medium bowl or a measuring cup, combine the buttermilk, vegetable oil, rum (if using), and the vanilla.
Step 5
Gently beat in one-third of the flour mixture. Before it’s fully combined, add half of the buttermilk mixture. Repeat with another one-third of the flour and the remaining buttermilk, and end with the remaining flour, beating until everything is well blended and no lumps remain.
Step 6
Pour the cake batter over the prepared pineapple and smooth the top. Bake until the cake is golden brown, pulling away from the sides of the pan, and the top springs back ever so slightly when pressed, 40–45 minutes.
Step 7
Remove the cake from the oven and let it cool for 5–10 minutes before inverting it onto a large plate or platter, using a butter knife or offset spatula to coax it from the pan if needed.
