Pineapple Upside-Down Cake

Retro-favorite pineapple-upside down cake gets an easy upgrade courtesy of sophisticated Luxardo cherries in this recipe from cookbook author Cheryl Day. Deeply fruity and so-red-they’re-almost-black, Luxardos pack way more flavor than the saccharine, candy-colored maraschinos seen in many other iterations of this classic dessert. But don’t get too fancy: There’s no need to break down a whole pineapple here. While we do believe there is a time and place for fresh pineapple, this cake calls for canned pineapple rings, which are uniform in shape, always juicy, and never out of season. For the best flavor, look for rings packed in 100% pineapple juice.

If you’ve never flipped a cake before, you’re in for a treat. “The surprise when you unmold the cake,” writes Day in her cookbook Cheryl Day’s Treasury of Southern Baking, “is what makes [baking this style of dessert] so satisfying.” Expect a mosaic-like display of fruit arranged artfully, but effortlessly, on top of the cake, glazed with a caramelly topping of melted butter and brown sugar that keeps the dessert supremely moist and unabashedly delicious. A few things to keep in mind: Make sure your serving plate is wider than the cake pan; wait until the pan has cooled slightly; and invert with gusto, which helps ensure nothing will stick to the bottom of the pan.

Editor’s note: This recipe was originally published in October 2021.

Place a rack in middle of oven and preheat to 350°. Place a 13×9″ metal baking pan by the stove. Cook brown sugar, butter, vanilla extract, and salt in a small saucepan over medium heat, stirring occasionally, until butter is melted and mixture is bubbling, about 5 minutes. Pour caramel into baking pan and spread to evenly coat bottom with a heatproof rubber spatula, nudging into corners.

Arrange pineapple slices on top of caramel without overlapping. Place a cherry in the center of each pineapple ring. Set aside.

Whisk flour, baking powder, salt, and mace in a medium bowl. Whisk eggs and vanilla extract in a small bowl.

Beat butter and granulated sugar in the bowl of a stand mixer fitted with paddle attachment on medium-high speed until light and fluffy, about 4 minutes. Add egg mixture in 4 batches, beating on medium speed 30 seconds after each addition and scraping down bowl as needed. Reduce mixer speed to low and beat in dry ingredients in 3 additions, alternating with sour cream in 2 additions, mixing 30 seconds after each addition. Fold batter a few times with a clean spatula, scraping down sides to make sure everything is well mixed. Scrape batter into reserved baking pan; smooth surface.