Place Oreo cookies into food processor and pulse into fine crumbs.
Add milk and instant pudding mix to a large bowl. Whisk until smooth and thickened. Let sit about 5 minutes.
Use a rubber spatula and fold the whipped topping into the pudding mixture until well combined.
Add 2 tablespoons of crushed Oreos to the bottom of five 8 oz cups. Then add 3 tablespoons of pudding on top.
Add another layer of crushed Oreos and then another layer of pudding. Top with more crushed Oreos.
Place 3 gummy worms on top. Chill for one hour, or until ready to serve.
If making Halloween dirt cups: After completing the steps above, you can take a Milano cookie and write RIP using black icing. Then stick it into the pudding so it stands up like a gravestone. Sprinkle a few candy eyeballs around.