Add the Oreo cookies to a large zip-top bag and crush them with a rolling pin until you have fine crumbs with a few small chunks. Alternatively, pulse them in a food processor, leaving a bit of texture so the topping isn’t too powdery.

In a medium bowl, combine about 2/3 of the crushed Oreos with the melted butter and stir until evenly moistened. Press this mixture firmly into the bottom of a 9x13-inch pan to form a loose crust. Use the bottom of a measuring cup to help press it into an even layer.

In a large mixing bowl, beat the softened cream cheese with a hand mixer until smooth and fluffy. Add the powdered sugar, vanilla extract, and a pinch of salt. Beat again until creamy and well combined, scraping down the sides of the bowl as needed.

Gently fold in half of the whipped topping (about 6 oz) into the cream cheese mixture using a spatula and light sweeping motions to keep it airy. This becomes the first creamy layer.

Spoon the cream cheese mixture over the Oreo base and spread it into an even layer with an offset spatula or the back of a spoon. Try not to disturb the cookie base too much.

In a separate large bowl, whisk together the cold milk and the instant chocolate pudding mixes for about 2 minutes, or until thickened. Let the mixture sit for 3–5 minutes to firm up; it should be thick but spreadable, like soft yogurt.

Gently pour or scoop the thickened pudding over the cream cheese layer and spread it evenly from edge to edge to create the chocolate layer.

Spread the remaining whipped topping over the pudding layer using gentle strokes so you don’t pull the pudding up into the topping. Optionally, create decorative swoops on the surface with the back of a spoon.

Sprinkle the remaining crushed Oreos evenly over the top to resemble “dirt.” If desired, tuck gummy worms or chocolate rocks into the crumbs for a classic dirt-cake look.

Cover the pan with plastic wrap or a lid and refrigerate for at least 4 hours, or overnight, until the layers are fully set and chilled.

Slice into squares with a sharp knife, wiping the blade between cuts for neat edges. Serve cold straight from the fridge.