This crowd-pleasing dessert pairs sweet fruit and moist, buttery cake. Here, the canned pineapple has been swapped out for fresh for a brighter taste.
1 (18 oz) container cored pineapple
11 tbsp butter, room temperature and divided
1/2 cup packed light brown sugar
1 1/2 cups all-purpose flour
2 tsp baking powder
1/4 tsp salt
1 cup granulated sugar
3 large eggs
1 tbsp vanilla extract
1/2 cup whole milk
Preheat oven to 350°F. Cut the pineapple into 7 thin rings.
In a 10- to 12-inch oven-safe skillet, melt 3 tbsp butter on medium, swirling occasionally. Sprinkle the brown sugar over the butter and cook 1 min. Remove from heat. Arrange pineapple rings in skillet.
In a large bowl, whisk the flour, baking powder, and salt. In a separate bowl, with a hand mixer or stand mixer, beat the remaining 8 tbsp butter and granulated sugar until fluffy. Beat in eggs, 1 at a time, then beat in vanilla until well blended. With mixer on low, beat in flour mixture and milk, alternating between, until just combined.
Pour cake batter over pineapple in skillet, gently spreading into an even layer. Bake 28–30 min., until toothpick inserted into center comes out clean. Cool cake on wire rack 15 min. Loosen sides of cake from pan.
Place a large serving plate over skillet. Carefully invert cake onto plate. Serve warm or at room temperature.
For the classic touch, garnish with maraschino cherries.