Crush the Cookies: Place cookies in a food processor and pulse until they resemble fine crumbs. Set aside.
Make the Creamy Filling: In a mixing bowl, beat cream cheese, butter, and powdered sugar until smooth.
Prepare the Pudding: In another bowl, whisk together pudding mix, milk, and vanilla extract until thickened.
Combine & Fold: Gently fold the pudding mixture into the cream cheese mixture, then fold in the whipped topping until well combined.
Layer the Cake: In a serving dish or individual cups, layer half of the crushed cookies, followed by the pudding mixture, then top with the remaining crushed cookies.
Decorate & Chill: Add gummy worms on top for a fun dirt effect. Refrigerate for at least 2 hours before serving.