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Pineapple Upside-Down Cake

Pineapple Upside-Down Cake

Created by Chef Dean

A buttery golden cake crowned with caramelized pineapple rings, jewel-bright cherries, and a lacquered brown sugar glaze that pools into sticky amber rivers when you flip it onto the plate.

Desserts
American
Potluck
Comfort Food
25 min
Active Time
50 min cook1 hr 15 min total
Yield8 servings

This cake arrived in American kitchens alongside a revolution in canned goods. When James Dole began shipping Hawaiian pineapple to the mainland in the early 1900s, home bakers discovered they could create something extraordinary with ingredients that kept in the pantry. By the 1920s, pineapple upside-down cake had become a national obsession.

The genius lives in the inversion. You build the topping first, arranging pineapple rings and cherries in a pool of melted butter and brown sugar. The batter goes on top. During baking, that sugar mixture transforms into a sticky caramel that penetrates the cake's surface while the fruit softens and concentrates. When you flip the pan onto a serving plate, the whole thing emerges gloriously bronzed, glistening, and utterly irresistible.

I insist on cast iron for this cake. The heavy pan distributes heat evenly, the caramel cooks without burning, and the drama of inverting a skillet at the table is worth the slight effort. This is a cake that demands to be served warm, with the caramel still slightly flowing, to people you genuinely like.

Ingredients

unsalted butter (for topping)

Quantity

6 tablespoons (85g)

dark brown sugar

Quantity

3/4 cup (165g)

packed

pineapple rings in juice

Quantity

1 can (20 ounces)

drained and patted dry

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