Preheat the oven to 350. 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 mix 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.