Line a tray or counter with paper towels. Place the pineapple slices (save the juice from the can!) and maraschino cherries on the paper towels. Let the moisture absorb for a few minutes, then flip them over and repeat. This step helps prevent the cake from becoming too wet.
20 oz can pineapple slices in juice
Preheat the oven to 350ºF. In a 9 inch round cake pan or 9 inch pie pan, add the melted butter and use a spatula to brush it over the sides and bottom. Sprinkle the brown sugar over the butter. It doesn’t need to be perfect because the brown sugar will melt while baking. Place a single whole pineapple slice and one maraschino cherry in the center of the pan. Cut a few pineapple slices in half. Line them around the outside, placing a maraschino cherry by each one. While you prepare the cake batter, refrigerate the pan for a few minutes. This helps to set the arrangement of the pineapple and cherries.
20 oz can pineapple slices in juice, 1/4 cup (57g) unsalted butter, 1/2 cup (107g) brown sugar, 13-19 maraschino cherries
Prepare the batter. In a mixing bowl combine the flour, baking powder and salt. Set aside.
In a separate mixing bowl combine the butter and granulated sugar, beat with an electric mixer on medium-high speed for 1 minute. Beat in the eggs and vanilla extract, about 30 seconds on medium speed.
1/2 cup (113g) unsalted butter, 3/4 cup (149g) granulated sugar, 2 large eggs, 1 tsp vanilla extract
Add the flour mixture, mixing on low. Add in the milk and pineapple juice, mix on low until combined.
1/4 cup (59ml) milk, 1/4 cup (59ml) pineapple juice
Remove the pan from the fridge and pour the batter evenly over the topping. Bake at 350ºF for 30 minutes. Then remove the pan and loosely cover it with foil. This is to help prevent the cake from over-browning. Return to the oven to bake for another 13-17 minutes or until a toothpick inserted in the center comes out mostly clean, a few crumbs are normal!
Allow the cake to cool for 20 minutes in the pan.
Run a knife along the edge of the pan. Place a large plate on top of the pan and flip. Tap the back of the pan if needed to help release. Allow the cake to cool before cutting and serving. Store leftover cake covered in the fridge.
Video
Notes
If you bake the cake in an 8" pan, it will result in a taller cake; however, the rings will be crowded together. During recipe testing I baked this in a 9 inch springform pan and some of the butter dripped through, so be aware of that if you use a springform pan.