In a large bowl, whisk together the instant chocolate pudding mix and cold milk. Continue whisking for about 2 minutes, or until the pudding begins to thicken. Let it sit for 5 minutes to set.

Gently fold the thawed whipped topping into the thickened chocolate pudding until well combined and smooth. Be careful not to overmix.

Reserve about 1/2 cup of the crushed chocolate sandwich cookies for garnish. Add the remaining crushed cookies to the pudding mixture and stir until just combined. This will give your pudding that signature 'dirt' texture.

Begin layering your dirt pudding. In your chosen serving dish (a trifle bowl, a 9x13 inch baking dish, or individual clear cups work wonderfully), start with a layer of the chocolate pudding and cookie mixture.

Add a layer of the reserved crushed cookies over the pudding. Continue layering the pudding mixture and crushed cookies, ending with a layer of crushed cookies on top.

Artfully arrange the gummy worms on top of the 'dirt' layer, letting some peek out as if they're burrowing. Chill in the refrigerator for at least 1 hour before serving to allow the flavors to meld and the pudding to set further.