In a small bowl, mix the graham cracker crumbs and melted butter until combined.
Press the mixture evenly into the bottoms of serving cups.
In a large bowl, beat the cream cheese, sugar, and vanilla extract until smooth.
In a separate bowl, whip the heavy cream until stiff peaks form, then gently fold into the cream cheese mixture.
Fold in the crushed pineapple until well incorporated.
Spoon the cheesecake filling over the crust in each cup and smooth the tops.
Refrigerate for at least 2 hours before serving.
Top with whipped cream and garnish with pineapple slices before serving.