Crush the Cookies: Finely crush about Ā¾ of the cookies in a food processor or by placing them in a sealed bag and rolling with a rolling pin. Set aside. Roughly chop the remaining cookies into chunks for topping.
Make the Peanut Butter Layer: In a large bowl, beat the softened butter, creamy peanut butter, powdered sugar, and vanilla extract until light, creamy, and fluffy. Set aside.
Make the Chocolate Pudding Layer: In another large bowl, beat the cream cheese until smooth. Gradually add cold milk and pudding mix, beating until thick. Fold in the thawed whipped topping until smooth and fully combined.
Assemble the Layers: In a 9×13-inch dish, spread half of the crushed cookie crumbs as the base layer (the ādirtā).
Spread the peanut butter mixture evenly over the cookie base.
Carefully spread the chocolate pudding mixture over the peanut butter layer.
Sprinkle the remaining crushed cookies and chunky pieces on top to resemble loose dirt.
Decorate: Add gummy worms peeking out of the ādirt.ā Stand up Milano cookies or graham crackers as gravestones, writing spooky messages like āRIPā using edible markers if desired. Add Halloween candies for extra frightful fun.
Chill: Refrigerate for at least 4 hours or overnight to let the layers set and flavors meld.
