Crush the Oreos: Place the cookies in a zip-top bag and crush with a rolling pin until you have fine crumbs with a few small chunks. Set aside.
You can also pulse them in a food processor.
Make the pudding: In a large bowl, whisk the instant pudding mix with cold milk for about 2 minutes until thick and smooth. Let it sit for a minute to set.
Optional cream cheese layer: If using, beat the softened cream cheese, powdered sugar, and vanilla until smooth. Fold in half of the whipped topping until creamy.
Fold in whipped topping: Gently fold the remaining whipped topping into the pudding until combined and fluffy.
If using the cream cheese mixture, you can layer it separately or fold it into the pudding for a thicker, mousse-like texture.
Layer the cups: Spoon a tablespoon or two of crushed Oreos into the bottom of each cup. Add a layer of pudding mixture. Repeat with more Oreos and more pudding, ending with a final “dirt” layer of cookie crumbs on top.
Decorate: Press a couple of gummy worms into the top layer.
Add any extra decorations you like, such as chocolate rocks or a sprig of mint for “plants.”
Serve or chill: These are ready to eat right away, but they’re even better after 20–30 minutes in the fridge. The layers settle, and the flavors meld.