Pineapple Upside Down Cake (Brown Sugar Bessy Version)

The pineapple upside down cake became popular when Dole hosted a pineapple recipe contest in the mid 1920s and received 2,500 recipes for this unique cake with a tropical star. This version of the beloved retro recipe relies on brown sugar throughout the cake for a standout maple flavor. Use either light or dark brown sugar to your liking; dark brown sugar will have a stronger maple flavor than light brown sugar.

A few other differences between this version and many classic versions are that I also use egg whites instead of whole eggs for a slightly different flavor and texture, and enjoy a generous amount of vanilla in mine!

I love the look of this cake with the spotlight on the beautiful, caramel-y deep yellow of the pineapples and the bright red maraschino cherries, too. Feel free to get creative and arrange the pineapples and cherries to your liking!



  • 56 g / 4 tbsp / 1/4 cup salted butter, melted
  • 3/4 cup light or dark brown sugar
  • 565 g / 20 oz canned sliced pineapple rings in juice
  • 12 – 20 maraschino cherries


  • 1 1/2 cups flour
  • 1 tsp baking powder
  • 1/4 tsp baking soda
  • 113 g / 4 tbsp / 1/2 cup salted butter, softened
  • 3/4 cup brown sugar
  • 2 large egg whites
  • 1/3 cup sour cream
  • 1 tbsp vanilla extract
  • 1/4 cup milk
  • 1/4 cup pineapple juice from the can



  1. Preheat oven to 350° F.
  2. For the topping, pour 1/4 cup of melted butter into 9″ x 2″ cake pan and brush butter up the sides.
  3. Sprinkle 3/4 cup brown sugar evenly over the butter in the pan.
  4. Arrange pineapple rings and cherries in the pan and then set the pan with toppings in the refrigerator while you prepare the cake batter.


  1. Whisk the flour mixture of flour, baking powder, and baking soda together and set aside.
  2. In another bowl, beat the butter until creamy, then slowly add the sugar in the mixture on medium speed. While still running the electric mixer, add the egg whites, then the sour cream, and then the vanilla. Add the dry flour mix next. Finally, turn the mixer to low speed and add the milk and pineapple juice.
  3. Once the batter is mixed well, remove the cake pan from the refrigerator and pour the cake mixture over the pan.
  4. Bake for 35-40 minutes, or until it passes the dry toothpick test.
  5. Let sit for 20 minutes before removing from the pan.
  6. Run a spatula or butter knife along the sides to help loosen, then turn the pan over onto a plate or serving platter, tapping as needed. Remain cool and confident when flipping 🙂

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