Preheat the oven to 350°F. Prepare 24 wells of a muffin tin by spraying with cooking spray.
In a large bowl, mix together the pineapple juice, yellow cake mix, oil, and eggs until well blended.
Cut each of the pineapple rings into four equal-sized pieces. Mix together the butter and brown sugar, and add about 1 teaspoon of the butter mixture to each well of the muffin tin. Add two pieces of pineapple and a maraschino cherry half, cut side up.
Pour the cake batter into the muffin tins, filling to about ¼ inch from the top. Bake 20-25 minutes or until golden brown. Remove from oven and let cool 15 minutes, then loosen the cupcakes from the sides of the muffin tin with a knife and invert onto a cooling rack.
Serve warm with freshly whipped cream, if desired.