Butter a 9x13 baking dish and set aside.
In the bowl of a food processor, crush chocolate sandwich cookies until cookies are evenly crumbled into small pieces.
Add two tablespoons of sugar and the melted butter and pulse until combined.
Press the cookie/butter mixture into the greased baking dish and place in the freezer for about 10 minutes to chill while you prepare the next layer.
With a hand mixer or whisk, beat together cream cheese, granulated sugar, and 3 tablespoons of heavy whipping cream until fluffy and combined. Add in 1 cup of the frozen whipped topping and combine.
Spread the cream cheese mixture over the chilled cookie crumbs and return baking dish into the freezer for another 10 minutes.
Beat or whisk together pudding mix, 2 ¼ cups of milk, and 1 additional cup of frozen whipped topping. Mix until mixture thickens.
Spread pudding layer over the chilled cream cheese layer.
Gently top with remaining whipped topping. Sprinkle with dark/mini/white chocolate chips, crushed Oreos or whatever else you'd like.
Chill in the refrigerator for at least 30 minutes to allow layers to firm up before serving.
Slice into squares and serve.