Preheat oven to 300°F.
For the crust: Crush graham crackers and drain the 20-ounce can of crushed pineapple.
Melt 1/2 cup salted butter in the microwave in a medium, microwave-safe bowl. Add 2 1/2 cups graham cracker crumbs to the melted butter and stir until combined.
Measure out 2 cups of the crumb mixture and press it firmly into the bottom of an 8×8-inch or 9×9-inch square baking dish. Bake the crumb mixture for about 8-10 minutes and then allow to cool completely. Reserve 1/2 cup of the crumb mixture for topping.
For the filling: In a stand mixer (or using an electric mixer), beat 4 ounces cream cheese and 1/2 cup butter until creamy.
If using a stand mixer, turn it down to low and add 2 cups powdered sugar slowly until it is all incorporated and smooth. Add a heaping tablespoon of the drained crushed pineapple and stir well.
Spread the cream cheese mixture over the baked and cooled graham cracker crust.
In a separate bowl, combine the 8-ounce container of frozen whipped topping with the remaining drained crushed pineapple. Stir well until thick and clumpy.
Spread the whipped topping mixture over the cream cheese layer by dropping it by the spoonful and then gently spreading it using the back of a spoon.
Sprinkle the reserved graham cracker crumb mixture on top. Cover the whole dish with plastic wrap. Refrigerate for at least 4 hours before slicing and serving. Enjoy the creamy, dreamy delight! 
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