Whisk together the instant vanilla pudding mix and 2 cups of whole milk in a medium bowl until thickened (about 2 minutes). In a separate bowl, whisk the instant chocolate pudding mix with the remaining 2 cups of whole milk until thickened. Cover both bowls and chill in the refrigerator for at least 5 minutes while you prepare other components.

Lighten with cream

Whip 1 cup of heavy cream with 2 tablespoons granulated sugar and 1 teaspoon vanilla extract until soft-medium peaks form. Gently fold half of the whipped cream into the vanilla pudding to create a lighter vanilla mousse, and fold the other half into the chocolate pudding to create chocolate mousse. Return to refrigerator.

Cream Layer

Make cream cheese filling

In a mixing bowl, beat the softened cream cheese until smooth. Gradually add the powdered sugar and continue to beat until fully incorporated and smooth. Fold in the remaining whipped topping (about 1 cup) by hand until the mixture is uniform and spreadable. Chill briefly if too soft.

Oreos & Assembly

Prepare Oreo crumbs

Reserve 8 whole Oreos for garnish. Place the remaining Oreos (about 16) in a large zip-top bag or food processor. Pulse or crush until you have fine crumbs with occasional small pieces. Mix the crumbs with 2 tablespoons melted butter until the texture holds together slightly when pressed.

Layer the cups

Divide the Oreo crumb mixture evenly among 8 serving cups (about 2–3 tablespoons per cup) and press gently to form an even bottom layer. Spoon or pipe the vanilla mousse over the crumbs into half of the cups and the chocolate mousse into the other half, filling each cup about 2/3 full. Add a generous layer (about 2 tablespoons) of the cream cheese filling on top of each pudding layer.

Top with crumbs and garnish

Crumble the reserved 8 Oreos and sprinkle evenly over the cream cheese layer of each cup. Sprinkle a few mini chocolate chips on top of each. If desired, top each cup with a whole Oreo half or a mint leaf for garnish. Chill the assembled dirt cups in the refrigerator for at least 1 hour (overnight is best) to set and let flavors meld.

Serve

Serve chilled. If you made them ahead, give each cup a gentle stir before serving if they’ve separated slightly, or refresh with an extra sprinkle of crumbs and a mint leaf.