First, make sure you have your whipped cream handy. If you're using canned whipped cream or Cool Whip, you're all set! If you'd prefer to make your own whipped cream, simply whisk together 1-½ cups of heavy cream, 2 teaspoons sugar, and 1 teaspoon vanilla extract. This will approximately equal 8 ounces of whipped cream topping.
Also, crush those Oreo cookies. You can accomplish this by mixing them up in a food processor, or just putting the cookies in a ziploc bag and hitting them with a rolling pin. No need to remove the cream centers, they'll get mixed into the crush.
16 Oreo cookies
To make the pudding, just whisk together the instant chocolate pudding mix and milk until it's all well blended and smooth. Then, let it rest for about 5 minutes so the pudding can thicken.
Two 3.9 ounce boxes of chocolate instant pudding mix, 4 cups cold milk
Once the pudding has thickened, fold in the whipped cream. If this thins out the pudding a bit, just place it in the refrigerator for an additional 5 minutes before assembling the dirt cups.
8 ounces whipped topping
To serve the dirt cups, use any small cups that you have handy. For my recipe, I used 8-ounce clear disposable cups so that you're able to see the layers from the side.
Place a few spoonfuls of pudding in the bottom of the cup. Then, sprinkle a layer of cookie crumbles on top. Repeat this layer once more.
Top the pudding cups with gummy worms, sticking the ends of the worms into the crushed cookies, so they appear to be crawling out of the "dirt."
18 gummy worms
Serve and enjoy!