Pineapple upside-down cake is a pineapple version of a popular cake where sugar and fruit are cooked in the bottom of a pan, then a silky cake batter is spread over the fruit, so once flipped over after it bakes, the fruit sits on top of the cake.
Pineapple upside-down cake is often rooted with the story of Dole Pineapple producing a contest for pineapple recipes after their invention of a pineapple ring cutting rig around 1925, but upside-down cakes have a history born before home ovens, when these “skillet cakes” were baked over a fire.
Pineapple upside-down cake’s popularity peaked in the 1950s (which is where it gets its retro reputation from), but it’s stuck around, becoming just as much of a classic because it’s so easy to make.
Key Steps for Pineapple Upside-Down Cake
Cook and cool the brown sugar topping before making the cake batter. Butter and light brown sugar make up the glaze that bakes at the bottom of this cake. It holds the pineapple and maraschino cherries in place once the cake has cooled. Do this step first before arranging the pineapple and cherries on top of the glaze.
Dollop, don’t pour the batter: The batter for this cake is quite thick! Avoid knocking the pineapple and topping around by scooping the batter into big dollops on top of the fruit and then gently spreading it out with a spatula.
Cool the cake slightly before removing from the pan. The hardest part of making pineapple upside-down cake is the maneuver which turns the bottom of the cake pan into the top of the cake. Cooling the baked cake slightly before flipping it allows the topping to cool and stick to the cake before turning out.
Canned Versus Fresh Pineapple
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