Prepare the Muffin Tin: Preheat the oven to 325°F (163°C). Line a muffin tin with cupcake liners or grease each cavity well to prevent sticking.

Create the Pineapple Topping: In a small saucepan, melt butter and brown sugar together until bubbly. Spoon a small amount of this caramelized mixture into each muffin tin.

Assemble the Fruit Layer: Cut pineapple rings into small segments to fit into the muffin tin. Place a piece of pineapple on top of the brown sugar mixture, then add a maraschino cherry in the center.

Prepare the Crust: Crush graham crackers into fine crumbs. Mix with melted butter and press a small amount into each muffin tin on top of the pineapple layer.

Make the Cheesecake Batter: Beat cream cheese and granulated sugar until smooth. Add eggs one at a time, mixing well after each addition. Stir in vanilla extract and sour cream until combined.

Fill the Muffin Tin: Spoon cheesecake batter over the crust and pineapple layers, filling each tin almost to the top.

Bake the Cheesecakes: Place the muffin tin in the oven and bake for 18-22 minutes, or until the centers are just set.

Cool and Chill: Allow the cheesecakes to cool to room temperature before refrigerating for at least 2 hours to set completely.

Unmold and Serve: Gently run a knife around the edges of each cheesecake and invert onto a serving plate. Enjoy chilled.