Combine the cookie crumbs and butter and toss together until incorporated. Press 2 cups of the crumb mixture firmly into an 9×9 square pan.
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 it is all mixed together.
Next add the can of pineapple and cool whip and stir in with a rubber spatula.
Spread the pineapple mixture over the crust.
Sprinkle the remaining cookie crumb mixture on top. Refrigerate for at least 4 hours, preferably overnight.
Feel free to top with fresh berries when serving, if desired.
Notes
We would not suggest replacing cool whip with whipped cream. Cool whip has a stability to it that whipped cream does not. Cool whip stays full and fluffy, while whipped cream is airred and will release the air quickly, making the whipped cream drop and become runny.