Add Oreos (filling included) to a food processor and blend until they reach a fine crumb. You can also place them in a large zip-top bag and crush them with a rolling pin.
19.1 ounce Oreos
Set aside 1/3 (around 9-10 cookies worth) of the Oreo mixture for the top of the cake. Press the remaining Oreo crumbs evenly into the bottom of a 13×9 pan.
With a hand mixer, combine the butter and cream cheese, beating until smooth and creamy, about 25-45 seconds.
Add the powdered sugar and vanilla extract, mixing to combine on low speed.
1 cup powdered sugar, 1 teaspoon vanilla extract
Fold the cool whip into the cream cheese mixture with a rubber spatula.
8 ounces Cool Whip
In a separate bowl, whisk together the milk and instant chocolate pudding until smooth and the mixture begins to slightly thicken. Allow the mixture to set in the refrigerator for about 10 minutes.
6.8 ounces instant chocolate pudding, 3 cups milk
Fold the cream cheese mixture into the pudding mixture.
Pour over the Oreo crust, spreading gently to evenly distribute.
Add the remaining Oreo crumbs evenly on top of the dessert.
Cover and refrigerate for at minimum 3 hours or overnight.
For the Tombstones and Ghosts
Melt the white chocolate over a double boiler or in the microwave on 50% power. White chocolate scorches easily, so slow is the best way to melt it.
12 ounces white chocolate chips
Place 2 pieces of wax paper on your work surface.
To create ghosts, add a spoonful of melted white chocolate to the first waxed paper sheet, then use the back of the spoon to drag some of the chocolate downward. Dip the end of a lollipop stick into melted chocolate then add to the ghost body, twirling it to bury it in chocolate. Add small candy eyeballs then put aside to set completely. You can use an edible marker to add eyebrows after they have set.
To create tombstones, you can simply write RIP on the cookies themselves, or make the tombstones gray like we did. To do so, tint the remaining melted white chocolate with a small amount of black gel food coloring. Dip 2/3 of the cookie into the gray chocolate then place on second sheet of wax paper. Repeat for all cookies and allow chocolate to set completely. Once set, write RIP on the cookies with black decorator gel.
7.5 ounces Milano cookies
Decorate cake with cookie tombstones, ghost pops, pumpkins, and eyeballs. See below.
Take the cream cheese and unsalted butter out ahead of time. Both need to be properly soft or the filling will be lumpy. You'll also want to thaw your Cool Whip before beginning.
Use instant pudding, not cook and serve. Cook and serve sets too firm for this.
White chocolate scorches easily. Melt it at 50% power or over a double boiler, slowly.
Decorate after the chill if you can. The cake is firmer by then and the tombstones sit more securely in the dirt.
If you don't have a double boiler, fill a saucepan halfway with water and bring it to a boil. Place a bowl on top that just fits, making sure the bowl doesn't touch the water. Put the white chocolate chips in the bowl and turn the heat down to a simmer. Let the chocolate begin to melt, stirring as it goes. When it can be stirred but there are still unmelted pieces, turn the heat off. The steam will finish melting it. Keep stirring until all the pieces are gone.