Crush the Oreo cookies into fine crumbs using a food processor, or place them in a sealed plastic bag and roll over them with a rolling pin. Reserve about 1 to 1 1/2 cups of crumbs for the final top layer.

Beat the softened butter, softened cream cheese, powdered sugar, and vanilla extract until the mixture is smooth, creamy, and free of visible lumps.

In a separate bowl, whisk the instant vanilla pudding mixes with the cold milk until thickened. Give the mixture a minute or two to set before combining it with the cream cheese mixture.

Fold the thickened pudding into the cream cheese mixture until evenly blended. Gently fold in the thawed whipped topping to keep the filling light and fluffy.

Spread about one-third of the cookie crumbs across the bottom of a 9 x 13-inch dish, deep trifle bowl, or clean flowerpot. Add half of the pudding mixture and smooth it into an even layer.

Add another layer of cookie crumbs, followed by the remaining pudding mixture. Finish with the reserved cookie crumbs, spreading them carefully so the entire surface looks like dark dirt.

Decorate the top with gummy worms, pressing some partially into the crumbs so they appear to crawl through the dirt. Cover the dish and refrigerate for at least 4 hours before serving, or chill overnight for the best texture.