Preheat oven to 300 F.
Melt butter in the microwave and allow to cool. Combine the crumbs and butter and toss together until incorporated. Press 2 cups of the crumb mixture firmly into an 9×9 square pan and bake for 8-10 minutes. Place on wire rack to cool.
Beat the cream cheese and butter together until creamy. Turn the mixer down to low and add the powdered sugar one cup at a time until incorporated. Turn up and beat well for a minute or so. Add a heaping tablespoon of the drained pineapple and stir in with a rubber spatula. Spread the cream cheese and pineapple mixture over the crust.
Fold the remaining pineapple into the Cool Whip and spread on top of the cream cheese mixture. Sprinkle the remaining graham cracker crumb mixture on top. Refrigerate for at least 4 hours, preferably overnight.