Place the Oreos in a zip-top bag and crush them with a rolling pin until they're fine crumbs with some small chunks. Set aside about ¼ of the crushed Oreos for the top layer.

In a large bowl, beat the softened cream cheese, butter, and powdered sugar together until smooth and fluffy. Fold in half of the whipped topping until well combined.

In another bowl, whisk the chocolate pudding mix with the cold milk for about 2 minutes until it thickens. Let it sit for 5 minutes to set completely.

Fold the remaining whipped topping into the pudding mixture until smooth and fluffy.

In a 9x13-inch pan, spread half of the crushed Oreos on the bottom. Layer half of the cream cheese mixture over the Oreos, then half of the pudding mixture. Repeat the layers with remaining Oreos (reserving some for the top), cream cheese mixture, and pudding mixture. Top with the reserved Oreo crumbs. Add gummy worms if using.

Cover and refrigerate for at least 2 hours, or overnight for best results. Serve cold straight from the pan.