Growing up I never particularly liked the traditional pineapple upside down cake my mom make. Then when I was a teenager she switched to this recipe, which uses crushed pineapple as opposed to the typical sliced pineapple rings. The texture is much more appealing to me — and the cup of brown sugar you mix in doesn’t hurt either!
For the Topping:
- 1 20-ounce can crushed pineapple
- ¼ cup (½ stick) butter
- 1 cup brown sugar
For the Cake:
- 1 ¼ cups sifted unbleached all-purpose flour
- 2/3 cup granulated sugar
- 2 teaspoons baking powder
- ½ teaspoon table salt
- ¼ teaspoon grated nutmeg
- 1/3 cup butter, softened
- ½ milk
- 1 teaspoon vanilla extract
- 1 egg
- Maraschino cherries
Preheat oven to 350 degrees. Drain the pineapple in a sieve.
Spray the bottom and sides of a 9-inch square or round baking pan with vegetable spray. Place the ¼ cup of butter in the baking pan. Place the pan in the preheated oven and allow the butter to melt. (Keep an eye on the butter. You don’t want it to brown/burn). When the butter is melted, carefully remove the pan to a heatproof surface. Add the brown sugar to the butter and blend together.
Spread the drained pineapple evenly over the sugar mixture, but do not mix. Be careful. Remember the pan is hot. Set the pan aside while you make the cake.
In a mixing bowl, sift together the flour, sugar, baking powder, salt, and nutmeg. Add the softened butter, milk, and vanilla. Beat with a hand mixer or stand mixer (using whisk attachment) on low speed for 1 ½ minutes. Add the egg and beat for another 1 ½ minutes.
If you like maraschino cherries in your pineapple upside down cake, press them gently into the pineapple mixture in the pan before adding the batter.
This batter is quite thick. Much thicker than a typical cake batter. Spread the batter evenly over the pineapple with a rubber spatula.
Bake the cake for 35-40 minutes or until a toothpick/skewer inserted into the middle of the cake comes out clean. Remove the cake from the oven, loosen the edges with a knife, and immediately but carefully invert the cake onto a platter. If any of the pineapple/brown sugar sticks to the pan, just carefully remove it from the pan and set it back on the inverted cake. No one will notice.
Let the cake cool before serving.