Classic Pineapple Upside-Down Cake

Classic Pineapple Upside-Down Cake
Classic Pineapple Upside-Down Cake

This Classic Pineapple Upside-Down Cake is inspired from my mom, Maudell Longwell.  It really is the classic “make ’em smile” cake.  You know me, I always encourage you to use the freshest ingredients, and by all-means, using fresh pineapple is great.  But, I’ve tried it both ways, and fresh can be a bit problematic…there is a lot of water that is released that compromises the cake.

There are adjustments that can be made, but honestly, getting good quality, canned sliced pineapple, in pineapple juice, yields a wonderful cake.   The cake is moist and tender, and the sugary pineapple on the top is amazing.   Be sure to use a nice high (2″) pie plate or round cake pan.   You and your guests will love this cake, no doubt!

5.0 from 1 reviews
Classic Pineapple Upside-Down Cake
Prep time
Cook time
Total time
This Classic Pineapple Upside-Down Cake has bee a favorite dessert for generations, and there's a good reason why. It's super delicious! This is really not hard to make. You'll need a 2-inch high cake pan, or pie pan, and the rest --- is cake! 100% Loon Approved!
Recipe type: Dessert
Cuisine: Dessert
Serves: 8
  • 6 tablespoon unsalted butter
  • ⅔ cup light brown sugar
  • About 10 sliced pineapple rings (canned or fresh) sure to save the juice, you'll need it later. If using fresh, you'll need to purchase some pineapple juice (you'll need ¼ cup for the cake)
  • Maraschino cherries (about 15)
  • 1 and ⅔ cups sifted all-purpose flour
  • ½ teaspoon baking powder
  • ¼ teaspoon baking soda
  • ½ teaspoon salt
  • ½ cup unsalted butter
  • ¾ cup light brown sugar
  • ¼ cup granulated sugar
  • 1 large egg, room temp
  • ¾ cup whole milk
  • ¼ cup pineapple juice
  • 1 tablespoon vanilla extract
  1. Pre-heat the oven to 350 F
  3. Melt the 6 T of butter in a microwave-safe bowl.
  4. Pour the melted butter into a 9-inch pie dish or cake pan (must be 2" tall).
  5. Sprinkle the brown sugar (2/3 cup) over the melted butter.
  6. Top with pineapple slices and then place cherries in the centers of the rings and in open spaces.
  8. In a medium bowl, mix together the flour, baking powder, baking soda, and salt.
  9. Melt the ½ cup of butter and then add to a large mixing bowl.
  10. Using your stand mixer, hand mixer, or a whisk, mix the sugars into the butter until well incorporated.
  11. Whisk in the egg, milk, pineapple juice, and vanilla extract.
  12. Slowly mix in the dry ingredients in the butter/sugar mixture until smooth.
  13. Pour batter into the prepared pan.
  14. Bake for 50 minutes, or until a toothpick comes out clean when stuck into the center of the cake.
  15. Let rest for 15 to 20 minutes.
  16. Invert cake on top of a cake stand or serving plate.
  17. Slice warm or at room temp.
  18. Great with ice cream, or whipped cream!
  19. Enjoy!!



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