Preheat the Oven: Set the oven to 325°F (or 350°F depending on desired texture). Line a 12-cup muffin pan with paper liners.

Make the Pineapple Base: In a small bowl, stir together brown sugar and melted butter. Spoon about 1 teaspoon of the mixture into the bottom of each cupcake liner. Place a pineapple chunk or slice over the sugar mixture, then add a cherry in the center (optional).

Prepare the Crust: In another bowl, combine graham cracker crumbs and melted butter. Press about 1 tablespoon of the mixture over the pineapple layer in each liner to form the crust.

Mix the Cheesecake Filling: Using a hand mixer or stand mixer, beat softened cream cheese until smooth. Add sugar and mix until combined. Beat in eggs one at a time, then stir in vanilla extract and sour cream. Mix until smooth and creamy.

Assemble and Bake: Spoon the cheesecake filling over each crust until nearly full. Bake for 18–22 minutes, or until the centers are set but still slightly jiggly.

Cool and Chill: Let cheesecakes cool in the pan at room temperature, then refrigerate for at least 2 hours or overnight.

Serve: Once chilled, carefully remove the liners and invert each cheesecake onto a serving plate so the pineapple is on top. Serve as is, or add optional garnishes like whipped cream or toasted coconut.