Grilled Pineapple Upside-Down Cake
When pineapple caramelizes, whether on the grill or in the oven, its bright, tart flavor mellows to something warm and sweet—a neat trick that has long been the calling card of traditional pineapple upside-down cake. My grandmother’s version, with its canned pineapple rings, was one of my dad’s all-time favorite sweets. It’s one of mine, too, but when I make it, I start with freshly grilled pineapple to double the caramelization effect and add a splash of bourbon to drive the point home.
Recipe information
Yield
makes one 10-inch cake / serves 8 to 10
Ingredients
Topping
Cake
Preparation
Topping
Step 1
Preheat the oven to 350°F.
Step 2
Heat a grill pan or cast-iron skillet over medium heat until hot. Place the pineapple rings in the pan 4 or 5 at a time and cook for about 2 minutes per side, until golden brown and slightly caramelized. Remove from the heat and set aside.
Step 3
Melt the butter in a 10-inch cast-iron skillet over medium heat. Sprinkle evenly with the brown sugar, bourbon, and salt and cook until the sugar dissolves, about 2 minutes. Arrange the grilled pineapple rings in a slightly overlapping layer over the butter and sugar. Remove from the heat while you mix the batter.
Cake
Step 4
Have all the ingredients at room temperature before you begin.
Step 5
Cream the sugar and butter in a large bowl with an electric mixer until light and fluffy, about 3 minutes (see Know-how, page 315). Add the eggs one at a time, beating well and scraping down the sides of the bowl after each addition.
Step 6
Combine the flour, baking powder, and salt in a large bowl and stir to mix.
Step 7
Add the flour mixture to the butter mixture in thirds, alternating with the milk and beginning and ending with the flour mixture, stopping to scrape down the bowl several times and stirring just until all is incorporated. Do not overmix. Add the vanilla and stir to mix.
Step 8
Carefully pour the batter over the pineapple in the skillet and spread evenly. Bake for 30 to 35 minutes, or until the cake is golden brown and a wooden skewer inserted in the center comes out clean.
Step 9
Remove the cake from the oven and let cool in the skillet for about 5 minutes. Run a small knife around the edge of the skillet and place a large serving plate upside down over the top. Invert the skillet to release the cake and topping onto the plate. Serve warm or completely cooled.
Sara’s Swaps
Step 10
When summer peaches, apricots, or plums are at their juiciest, make this a peach, apricot, or plum upside-down cake. Just substitute peeled, sliced ripe peaches, apricots, or plums for the pineapple and omit the grilling step. If using peaches, give a double whammy of sweet peach flavor by serving with Farm-Stand Peach Ice Cream (page 363).
Know-how: Cutting Fresh Pineapple Rings
Step 11
Trim the top and bottom of the pineapple to form flat surfaces. Set the pineapple right side up and peel from top to bottom in long strips, slicing along the contours of the fruit. Place the peeled pineapple on its side and slice into rounds about 1/2 inch thick. Cut the core from the center of each round using a 1-inch cookie cutter to make a ring.
Know-how: Making Homemade Brown Sugar
Step 12
If you don’t have brown sugar on hand, use a mix of granulated sugar and molasses. The ratio for light brown sugar is 1 tablespoon molasses for every 1 cup of sugar; double the molasses for dark brown sugar. Just stir the sugar and molasses together thoroughly and use as needed.
