Preheat your oven to 350°F (175°C) and grease a muffin tin.
In a saucepan over medium heat, melt 2 tablespoons of butter with 2 tablespoons of brown sugar until bubbly.
Pour the caramel mixture into each muffin tin cup, place a pineapple ring on top, and tuck in a cherry.
In a mixing bowl, cream together the remaining butter and granulated sugar until fluffy. Add eggs one at a time.
In another bowl, whisk together flour and baking powder; mix into wet ingredients with vanilla until smooth.
Spoon batter over each pineapple ring until three-quarters full. Bake for about 20 minutes or until golden brown.
Let cool for five minutes before flipping onto plates.
