In a medium bowl, combine graham cracker crumbs and granulated sugar until well mixed. Pour in melted butter and stir until the mixture resembles wet sand.

Carefully divide half of the graham cracker mixture into six small dessert glasses or jars. Press down the crumbs to form a compact layer.

In a large mixing bowl, beat softened cream cheese with an electric mixer on medium speed until smooth. Gradually add powdered sugar and vanilla extract, mixing until fluffy.

Gently fold the crushed pineapple into the cream cheese mixture using a spatula.

In a separate bowl, whip the heavy cream on high speed until stiff peaks form. Carefully fold the whipped cream into the cheesecake mixture.

Spoon half of the cheesecake filling over the crust layer in each glass, sprinkle remaining graham cracker mixture on top, then add the rest of the filling.

Cover each glass with plastic wrap and refrigerate for at least 4 hours, preferably overnight.