Place cookies in ziplock bag and crush well with rolling pin.
Scrape out crumbs and icing and put in a small mixing bowl.
Measure out about ½ cup crumbs to sprinkle the top of the dessert and set aside.
To remaining Oreo cookie crumbs add butter.
Stir well with a fork.
Mix well and press very firmly into a 9x13” baking dish.
Mix cream cheese, powdered sugar and 8-oz. of the cool whip in a large mixing bowl with an electric mixer.
Spread evenly onto cookie crumb mixture.
Mix chocolate pudding and milk with an electric mixer until thick.
(Start with about 1/2 cup milk and continue adding in smaller increments so chocolate pudding doesn't splash everywhere).
This may take 2-3 minutes.
Spread chocolate pudding evenly onto cream cheese layer.
Spread remaining cool whip on top of pudding layer.
Sprinkle with reserved cookie crumbs.
Place cherries on top.
Garnish with additional Oreo cookies if desired.
Refrigerate about 6 hours or overnight.
Or freeze about two hours before serving.
If freezing, remove 45 minutes to an hour before serving.