Pineapple Upside-Down Cake

Pineapple upside-down cake is the retro favorite that never went away — a tender butter cake baked over caramelized pineapple rings and maraschino cherries, then flipped to reveal a glistening, jewel-bright crown. It was born in the 1920s when canned pineapple became a pantry staple, and it has been a potluck and birthday favorite ever since. The flip is the whole show.

Why this recipe works: The cake batter is a simple, sturdy butter cake — rich enough to hold the weight of the fruit. The bottom of the pan gets a layer of butter and brown sugar that melts into a golden caramel as it bakes, soaking into the pineapple and the cake above it. When you flip it out, you get a glossy, caramel-glazed top that needs no frosting.

Key ingredients

• Pineapple rings: canned rings in juice — drained well.
• Maraschino cherries: the classic red dots; halved or whole.
• Butter and brown sugar: the caramel base.
• Butter cake batter: flour, butter, sugar, eggs, and buttermilk or milk.

Tips for the perfect flip

Drain the pineapple very well and pat it dry — extra juice makes the cake soggy and the caramel watery. Arrange the rings and cherries in the buttered, brown-sugared pan before adding the batter, pressing them gently into the sugar. Bake until golden and a toothpick comes out clean, then let the cake rest in the pan for exactly 5 to 10 minutes before inverting — too soon and the topping slides, too late and it sticks. Flip onto a plate and replace any fruit that stayed behind.

Variations and storage

Use peach halves or plums in place of the pineapple, add a spoonful of rum to the brown sugar, or scatter toasted pecans around the fruit. The cake is best the day it is made, served warm or at room temperature; leftovers keep 2 days covered at room temperature. Reheat slices briefly for that fresh-from-the-oven feel.

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