1. Crush and Divide the Cookies

Pulse the chocolate sandwich cookies, filling included, until they form fine crumbs. A few small pieces are fine, but large chunks make the bottom less even and the middle layer harder to spread over.

Measure and divide the crumbs into three portions: two cups for the bottom and one and a quarter cups each for the middle and top. Keep the top portion covered if holding it until serving time.

2. Make the Bottom Layer

Mix the two cups of bottom-layer crumbs with six tablespoons melted butter. Stir until the crumbs look evenly moistened, then distribute across the dish and press into a flat layer.

Use the bottom of a measuring cup or a spoon to press gently but firmly. Excessive compression can make a very hard base once chilled. Refrigerate while making the filling so the butter can begin to firm.

3. Beat the Cream Cheese Base

Beat softened cream cheese and the separate half cup of softened butter until smooth. Scrape the bottom and sides of the bowl, then add the powdered sugar and two teaspoons vanilla.

Beat until creamy and free of visible lumps. Start slowly when adding powdered sugar to avoid scattering it. The mixture should be cohesive, not oily or melted.

4. Prepare the Instant Pudding

In another bowl, whisk both packages of instant pudding mix with three cups cold whole milk for about two minutes. Let stand for roughly three minutes, or until thickened according to the product’s behavior.

Check the bottom of the bowl for dry powder. The pudding should be thick but still easy to fold into the cream cheese base. If it remains thin, confirm that the product is instant pudding and that the milk quantity was measured correctly.

5. Whip the Filling Cream

Beat one and a half cups cold heavy cream in a chilled or cool bowl until firm peaks form. Stop when the cream holds its shape but still looks smooth. Overbeating can make it grainy and eventually turn it toward butter.

If using the whipped topping alternative, thaw it in the refrigerator and fold it in directly. Do not beat thawed topping as though it were liquid cream. The alternate version may be sweeter and have a different yield.

6. Combine the Filling

Add the pudding to the cream cheese base gradually, stirring or mixing gently until smooth. Fold in the whipped cream with a flexible spatula, lifting from the bottom and turning the bowl as you work.

Use enough strokes to combine thoroughly without beating away the air. If adding internal holiday jimmies, fold them in briefly at the end. Save delicate nonpareils for decoration.

7. Build the Middle Layers

Spread half the filling over the chilled cookie base. Add small dollops across the surface, then connect them gently with a spatula instead of dragging one large mound from the center to the edges.

Sprinkle one and a quarter cups dry crumbs evenly over the filling. Spoon the remaining filling on top in several places and spread carefully. It is fine if a few crumbs move into the cream; the dessert does not require perfectly sharp stripes to taste good.

8. Add or Reserve the Top Crumbs

For a softer, fully melded dirt layer, add the remaining one and a quarter cups crumbs now. For a fresher, looser surface, reserve them in a covered dry container and sprinkle on shortly before decorating.

Choose one approach and allocate the crumbs accordingly. Do not use the reserved top crumbs in the middle and then expect to have another full layer available later.

9. Cover and Chill

Cover the dish without pressing wrap into the filling and refrigerate at 40°F or below for at least four hours. Overnight chilling is convenient and gives the crumb and pudding layers more time to settle together.

This rest is part of the recipe, not an optional shortcut for the same texture. If served immediately, the mixture will be much softer and the layers less distinct.

10. Whip the Topping

Near serving time, beat the separate cup of cold heavy cream with three tablespoons powdered sugar and half a teaspoon vanilla until it holds firm peaks. Pipe or spoon onto the chilled dessert.

If the top crumbs were reserved, add them first. Make nine to twelve larger swirls or smaller dollops according to your planned servings. For more portions, use less cream per dollop or offer some pieces without individual swirls.

11. Decorate and Serve

Add holiday sprinkles, optional red icing, and garnish cookies close to serving. Press cookies into the cream only enough to support them. Heavy cookies can tip tall, narrow whipped cream cones, so a broader swirl is often easier to manage.

Serve cold using a dessert spatula or spoon. Wipe the utensil between portions if you want cleaner edges. Expect a creamy layered scoop rather than a rigid slice.