Crush the cookies: Place the cookies in a large zip-top bag. Crush with a rolling pin until they resemble fine crumbs with a few small chunks.
You want that dirt texture.
Whisk the pudding: In a large bowl, whisk the instant pudding mix with cold milk for about 2 minutes until it thickens. Set aside to firm up slightly.
Make the cream layer: In a separate bowl, beat softened cream cheese, powdered sugar, butter (if using), and vanilla until smooth and fluffy. No lumps.
Fold in the whipped topping: Gently fold the whipped topping into the cream cheese mixture until fully combined.
Don’t overmix—keep it airy.
Combine with pudding: Fold the chocolate pudding into the cream mixture until it’s even in color. You’re aiming for a light, mousse-like texture.
Layer the “dirt” and filling: In a 9x13 pan, trifle dish, or clear bowl, sprinkle a layer of crushed cookies on the bottom. Spread half the pudding-cream mixture over it.
Add another layer of cookies, then the remaining cream mixture, and finish with a thick layer of cookie crumbs on top.
Chill: Cover and refrigerate for at least 2–4 hours, or overnight if you can. This helps it set and deepens the flavor.
Decorate: Just before serving, press gummy worms into the top “soil.” Add candy bones, eyes, pumpkin candies, and chocolate rocks. If using green coconut “grass,” sprinkle it around a few candy tombstones for a graveyard vibe.
Serve cold: Scoop into bowls with a big spoon.
Add extra worms for good measure.