Add instant pudding to a large bowl with milk. With a hand mixer, blend until it stiffens.
Add cocoa powder, vanilla, cream cheese and powdered sugar. Mix until lumps are gone.
Add cool whip and mix again until creamy and smooth. Set aside.
Take 1 bag of oreo cookies and add to a large zip loc bag, let the air out and seal shut. With a rolling pin, crush the oreos until they are crumbled into little pieces. This will take a couple minutes. Or you can add to a food processor and pulse to get this texture. It's not fine crumbs, but little chunks of cookies AND crumbles.
In a 13x9 clear baking dish, add a layer of crumbles, so you don't see the bottom of the dish.
Take a few spoonfuls of the cream mix and place throughout the cookie crumbs. You need to slowly and gently spread the mix so you don't disturb the cookie crumbles. It's about half the mix.
Add another layer of the cookie crumbles over the cream mix until you can't see the cream mix. You might need to crush more cookies, that's why I have 2 bags of oreos in the recipe.
Add another layer of the cream mix and top with more cookie crumbles. I save a cookie to garnish so people know it's an oreo dish.
Cover with foil and refridgerate for 5 hours or over night.
You will be labeling out spoonfuls of this dish as servings. You can't cut it into pieces, Just spoon it out into a bowl!
You can do chocolate pudding if you'd like, but i like the contrast of colors because you can see the layers in the dish. I don't like to over power the chocolate flavor of the oreos.
