Pineapple Upside Down Cake
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When it comes to classic desserts it doesn’t get more classic than pineapple upside down cake. During the 1920s an influx of canned foods, including some from exotic tropical locations, made cooking even easier. And, the US became obsessed with pineapple- something that had never been that big of a deal before. Suddenly every cookbook and women’s magazine suddenly had recipes for pineapple fluff, ambrosia with pineapple, and other recipes for this citrus-y fruit.
A recipe contest held by the company that later became Dole in 1925 had 2,500 entries for pineapple upside down cake! It seems people have been enjoying this iconic cake for around a century. However, it became even more popular in the 1950s and the cheerful look of the cake, dotted with red maraschino cherries, became highly associated with the decade.

To begin this recipe it’s best to place your pineapple slices and cherries on some paper towels and pat them dry. Then line your cake pan with melted butter and brown sugar. Arrange the pineapple rings along the bottom and sides of the pan. I find it’s easiest to cut a few of them in half for the sides.
Then place the cherries in the holes of the pineapple rings. I like to also fill in a few of the gaps with cherries, too.

Then start on the rich batter, which has sour cream in it for a lovely flavor. It’s thick which helps you to pour it on slowly over the fruit. You don’t want to disturb the pineapple, but I do like to take a butter knife and push the batter into all the nooks and crannies at the sides.
Then bake this cake for 30 minutes uncovered. After that loosely tent it with foil to keep the bottom from getting too brown during the last 15 minutes of baking.

Some sources say you only need to let this cake cool for 30 minutes, but in my experience it will need at least 1 hour to cool off. However, don’t put it in the fridge since you want it room temperature when it’s time to cut into slices.

This classic pineapple upside down cake is a slice of history that has stood the test of time because it’s so delicious. The buttery sweet topping, the bright taste of pineapple, the vanilla cake, and the sweet cherries are a truly irresistible combination.
Pineapple Upside Down Cake
For the topping:
- 1 (20 oz) can pineapple slices in juice, with juice reserved
- 16-20 maraschino cherries
- 4 tablespoons unsalted butter, melted
- 1/2 cup brown sugar
For the cake batter:
- 1 1/2 cups all-purpose flour
- 1 teaspoon baking powder
- 1/4 teaspoon baking soda
- 1/4 teaspoon salt
- 1 cup whole milk
- 1 tablespoon apple cider vinegar
- 1/4 cup reserved pineapple juice
- 1/4 cup sour cream
- 1 1/2 teaspoons vanilla extract
- 1 stick unsalted butter, softened
- 3/4 cup granulated sugar
Preparation
- Preheat oven to 360˚F. Drain pineapple and set aside juice. Lay pineapple and cherries on paper towels and pat dry. Pour melted butter into a 9” round pan that’s at least 2 inches deep. Swirl pan to coat with butter, making sure sides are coated as well. Sprinkle pan with brown sugar. Line pan with pineapple rings and place a cherry in the center of each one and between the rings as well. Set aside.
- In a large bowl combine dry ingredients for batter. Set aside. In a separate bowl combine milk, pineapple juice, sour cream, and vanilla. In another large bowl cream together butter and sugar.
- Add 1/3 of the flour mixture and 1/3 of the milk mixture to the sugar mixture. Repeat until dough is thick and smooth. If any pineapple pieces didn’t fit into the bottom of the pan chop them small and fold them into the batter.
- Pour batter into pan slowly and then bake for 30 minutes. Add foil to pan to loosely tent cake and return to oven to bake for another 15 minutes. Allow to cool for at least 1 hour. Run a knife along the edge of the cake. Place a plate on top of pan. Flip pan over so that pineapple pieces are on top and slice into 10-12 pieces.
Recipe adapted from Recipe Tin Eats.
