Whip the cream cheese and butter until smooth. Add the sugar and vanilla and mix until incorporated.
Add the milk and pudding and mix together. Chill until set about 15 minutes.
Fold in the Cool Whip after the pudding is set.
In a large bowl or trifle dish. Spoon in a layer of pudding mixture the top with a layer of crushed Oreos. Repeat layers. You can make as many layers as you want.
Top with a big dollop of Cool Whip and garnish as desired.
Chill 30 minutes to 2 hours before serving.
Cover tightly and store up to 2 days in the refrigerator.