Pour 1/4 cup melted butter into the cake pan. Swirl the pan until the bottom and the inside sides of the cake pan are well-coated with the butter to prevent the cake from sticking. Sprinkle the brown sugar evenly over the melted butter. Arrange the pineapple slices on top of the brown sugar. Place the maraschino cherries in the center of each of the pineapple rings. Add more as you prefer.
Make the cake:
Whisk together the flour, baking powder, baking soda, salt, and sugar together in a large mixing bowl. Set aside.
Whisk together the buttermilk, remaining 1/4 cup of melted butter, pineapple juice, eggs, and vanilla extract in a separate bowl or large measuring cup. Whisk into the flour mixture until well combined. Stir in the leftover chopped pineapple.
Pour the cake batter over the pineapple and cherry topping. Spread the cake batter in the pan with an offset spatula or the back of a spoon.
Place in the oven and bake for approximately 45 minutes to 1 hour or until a toothpick or skewer inserted in the center comes out clean. You can follow my tips for how to tell when your cake is done.
Remove the cake from the oven and allow to stand for about 5-10 minutes before transferring to a cake stand.
Run a butter knife or offset spatula around the edges of the cake in the cake pan to make sure the cake has released from the pan. Place the cake plate (or cake stand) on top of the cake pan. Carefully invert the cake pan and cake cake plate. Place the cake plate onto a solid surface such as your countertop. Then, lift the cake pan straight up off of the cake plate.
Notes
Storage Tips
To store. While you can store this cake at room temperature for a day or so, I recommend storing the cake covered in the refrigerator for up to 5 days. To serve, allow to reach room temperature before serving. To make ahead. Prepare the cake according to the recipe instructions. Cool the cake completely and cover the cake plate. Store in the refrigerator for up to 5 days. To freeze. Cool the cake completely and wrap it or individual slices tightly with plastic wrap topped with foil. Store in a freezer-safe container in the freezer for up to 3 months. To serve, allow to thaw overnight in the refrigerator. Then, remove from the refrigerator and allow to reach room temperature before serving.