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Preheat oven to 350°F.
In a cast iron skillet or baking pan, spread the melted ½ stick of butter and 1 ⅓ cups of brown sugar evenly on the bottom.
Arrange the pineapple slices in a single layer on top of the brown sugar mixture. Sprinkle the drained crushed pineapple on top.
Place maraschino cherries in the center of the pineapple slices.
In a stand mixer, cream the 1 ½ sticks of unsalted butter and 1 ½ cups of sugar until light and fluffy.
Add the eggs one at a time, mixing well after each addition.
In a separate bowl, whisk together the 2 ½ cups of all-purpose flour, 1 tbsp baking powder, and 1 tsp salt.
Alternately add the ¾ cup of pineapple juice and ¾ cup of whole milk to the butter mixture, mixing just until combined after each addition.
Fold in the dry ingredients until just combined, being careful not to overmix.
Pour the batter over the pineapple mixture in the skillet.
Bake for 30-40 minutes, until a toothpick inserted in the center comes out clean.
Allow the cake to cool in the pan for 5 minutes, then invert onto a serving plate.