In a bowl, combine crushed pineapple, granulated sugar, melted butter, and graham cracker crumbs. Press this mixture into the bottom of a 9x13 inch baking dish.
In another bowl, beat the softened cream cheese until smooth. Gradually add the powdered sugar and vanilla extract, beating until well combined.
In a separate bowl, whip the heavy cream until stiff peaks form. Gently fold the whipped cream into the cream cheese mixture.
Spread the cream cheese mixture evenly over the crust in the baking dish.
Chill for at least 2 hours before serving. Garnish as desired.
Notes
For an extra touch, you can top with whipped cream and maraschino cherries before serving.