Place the chocolate cookies in a zip-top bag and crush them into fine crumbs using a rolling pin or the bottom of a glass.
24 cookies chocolate sandwich cookies
In a large mixing bowl, whisk together the vanilla pudding mix and milk until smooth and slightly thickened, about 2 minutes.
3 cups milk, 1 package vanilla instant pudding mix
In a separate bowl, whip the heavy cream with sugar until soft peaks form and the mixture is fluffy.
2 cups heavy cream, 1/2 cup granulated sugar
Gently fold the whipped cream into the pudding mixture until well combined, creating a creamy filling.
1 package vanilla instant pudding mix, 2 cups heavy cream
Spread a layer of crushed cookies evenly across the bottom of your serving dish to resemble dirt.
24 cookies chocolate sandwich cookies
Pour half of the creamy pudding mixture over the cookie layer, spreading smoothly with a spatula.
1 package vanilla instant pudding mix
Add another layer of crushed cookies on top of the pudding layer for added texture.
24 cookies chocolate sandwich cookies
Top with the remaining pudding mixture, smoothing the surface for a uniform appearance.
1 package vanilla instant pudding mix
Decorate the top with gummy worms, poking them into the pudding so they appear to be wriggling through the dirt.
Gummy worms gummy worms
Chill the dirt cake in the refrigerator for at least 2 hours before serving, allowing flavors to meld and the pudding to set.
Serve cold, scooping out portions that reveal the layers of cookie crumbs, pudding, and playful gummy worms.