Preheat the oven to 300°F. (For a no-bake alternative, refrigerate the crust mixture for 20 minutes instead of baking.) Gently melt the butter and allow it to cool slightly. Blend the graham cracker crumbs with the melted butter until evenly moistened. Press 2 cups of this mixture into the bottom of a 9×9-inch square pan and bake for 8 to 10 minutes. Remove and let it cool on a wire rack.

In a mixing bowl, beat the softened cream cheese together with ½ cup softened butter until the texture becomes smooth and creamy. With the mixer on low, gradually add in the powdered sugar, one cup at a time, mixing thoroughly. Increase speed briefly to whip the mixture until light. Stir in one heaping tablespoon of the drained pineapple using a rubber spatula, then evenly spread this layer over the cooled crust.

Fold the remaining drained pineapple into the Cool Whip until well combined. Spread this pineapple whipped topping gently over the cream cheese layer. Sprinkle the remaining ½ cup of the graham cracker crumb mixture across the surface. Place the pan in the refrigerator and chill for a minimum of 4 hours, or ideally overnight, to allow the dessert to set fully.