Fresh Pineapple Upside-Down Cake

Popularized in the 1920s, pineapple upside-down cake first gained notoriety when James Drummond Dole’s Hawaiian Pineapple Company (now food giant Dole) sought to market canned pineapple to the American public. The original was pretty much what you’ll often find today: a yellow cake topped with syrupy-sweet pineapple rings, the center of each dotted with a DayGlo-red maraschino cherry. The trick, of course, is that the fruit is arranged in the pan before the cake batter is added. The whole thing is flipped after baking so the top of the cake is drenched in the syrupy combination of pineapple juice, melted butter, and brown sugar that pools in the bottom of the pan.

This pineapple upside-down cake recipe rehabilitates the retro American dessert by swapping out the usual canned fruit and using fresh, flavorful pineapple slices instead. In the ’20s, fresh pineapple was harder to access in the US, but now you can make this cake with fresh fruit for a brighter flavor—all you need to do is peel and cut the pineapple into slices and remove the fibrous core from each round. If you have ring cutters, you can use them to make the traditional ring shape; to keep things simple, you can also simply cut the fruit into half-circles. This recipe skips the cherries entirely, but if you’d like, buy some really good cocktail cherries and use them here for an upgrade that stays true to the classic colorful look.

The key to the best pineapple upside-down cake is to keep the caramelized pineapple from sticking to the pan. Just be sure to give the cake enough time to cool so that the buttery glaze is no longer bubbling hot—though you do want to flip it while that syrup is still warm. Set your kitchen timer and remember to turn the cake onto a plate big enough to catch any drips. Serve with vanilla ice cream or a dollop of tangy sour-cream-spiked whipped cream to balance the sweetness.