Preheat oven to 350°F (175°C). Line a muffin pan with paper liners.
Spoon about 1 teaspoon melted butter into the bottom of each liner.
Add about 1 tablespoon brown sugar to each, followed by one cherry in the center and a spoonful of crushed pineapple around it.
Place one vanilla wafer flat side down on top of the pineapple in each cup.
In a medium bowl, beat cream cheese until smooth. Add granulated sugar, eggs, and vanilla extract. Beat until creamy and smooth.
Spoon the cream cheese mixture over the wafers, filling each cup almost to the top.
Bake for 20–25 minutes or until set. Cool in the pan for 10 minutes, then refrigerate at least 2 hours.
Carefully remove the liners and invert each cheesecake to serve with the pineapple on top.