In a small saucepan, melt 0.25 cup butter over medium heat, and add the brown sugar. Stir until dissolved. Pour the mixture evenly into a 9-inch round cake pan.
Arrange pineapple slices over the brown sugar mixture in the pan, and place a maraschino cherry in the center of each slice.
In a large mixing bowl, whisk together flour, granulated sugar, baking powder, and salt.
In another bowl, combine the melted butter, milk, vanilla extract, and eggs. Beat until smooth.
Pour the wet mixture into the dry ingredients, and stir until just combined. Do not overmix.
Pour the batter over the pineapple slices in the cake pan, spreading it evenly.
Bake for 40-45 minutes, or until a toothpick inserted into the center comes out clean.
Let the cake cool in the pan for 5 minutes, then invert it onto a serving plate.
Notes
Serve warm with a scoop of vanilla ice cream for an extra delicious treat.