Crush all the Oreos in a large resealable plastic bag or in the food processor until they are crumbs. Press two-thirds of the crushed cookies into the bottom of a 9×13-inch baking dish and set aside. Reserve the remaining crushed Oreos.

In a large bowl, beat cream cheese and butter with a hand mixer until smooth. Mix in powdered sugar. Fold in whipped topping until well combined and set aside.

In a separate bowl, mix pudding, milk, and vanilla. Let sit until thickened. Fold this mixture into the cream cheese mixture.

Carefully pour the pudding/cream cheese mixture over the crumb crust in the pan.

Sprinkle with the reserved crushed Oreos. Refrigerate for 3-4 hours before serving.