Prepare the Oreo Crust: Place the Oreos in a food processor and pulse until finely crushed, resembling sand. In a greased 9x13 pan, spread one-third of the Oreo crumbs evenly across the bottom and pack down firmly using the back of a fork to create a solid crust.

Create Peanut Butter Layer: In a mixing bowl, beat the cream cheese with a hand mixer until smooth and creamy, about 2 minutes. Gradually mix in the instant vanilla pudding and creamy peanut butter until combined. Slowly add milk until the mixture is smooth and spreadable. Layer this peanut butter mixture over the prepared Oreo crust.

Layer Again: Sprinkle the remaining one-third of the crushed Oreos over the peanut butter layer, ensuring even distribution. Press the crumbs down to create a cohesive layer.

Make Chocolate Layer: In a clean mixing bowl, blend the cream cheese with the instant chocolate pudding until smooth, about 2 minutes. Melt the milk chocolate chips in a microwave-safe bowl (about 30 seconds on high, stirring until melted). Combine the cooled chocolate mix with the cream cheese mixture and gradually add in milk. Spread this chocolate layer over the Oreo layer.

Final Layer and Chill: Top the chocolate layer with the remaining crushed Oreos. Spread the whipped topping over the chocolate layer, cover, and chill in the refrigerator for 4-6 hours.