In a large bowl and using a hand-held mixer, mix the cream cheese and butter until creamy.
Add in 2 cups of confectioners sugar and mix again until fully combined.
Add in the whipped topping (cool whip) and the crushed pineapple. Using a spatula, gently mix until fully incorporated.
In a 10x 15 casserole dish (or 9x13 dish, but nothing smaller) that has been sprayed with non-stick spray, add 3 cups of the graham cracker crumbs. (You should have 1 cup remaining.) Press until flat and even.
Pour the filling onto the crust and spread in an even layer.
Sprinkle the remaining graham cracker crumbs over top.
Refrigerate for at least 2 hours, preferably overnight.