Preheat your oven to 350°F (175°C). Grease and flour a 9-inch round cake pan.
For the topping: Melt 0.5 cup of butter in a small saucepan and pour it into the prepared cake pan. Sprinkle evenly with 1 cup of packed brown sugar. Arrange the drained pineapple rings over the brown sugar mixture. Place a maraschino cherry in the center of each pineapple ring, if desired.
For the cake: In a large bowl, whisk together 1.5 cups of all-purpose flour, 1 cup of granulated sugar, 2 teaspoons of baking powder, and 0.5 teaspoon of salt.
In a separate bowl, cream 0.5 cup of softened butter until light and fluffy. Beat in the 2 large eggs one at a time, then stir in 1 teaspoon of vanilla extract.
Gradually add the dry ingredients to the wet ingredients, alternating with 0.5 cup of milk, beginning and ending with the dry ingredients. Mix until just combined. Do not overmix.
Gently spread the cake batter evenly over the pineapple and brown sugar topping in the prepared pan.
Bake for 40-45 minutes, or until a wooden skewer inserted into the center of the cake comes out clean.
Let the cake cool in the pan for about 10 minutes before inverting it onto a serving platter. Serve warm.
Notes
This cake is best served warm, but can also be enjoyed at room temperature. It pairs wonderfully with whipped cream or vanilla ice cream.