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Step 1
Place cookies in a resealable plastic bag; using a rolling pin, finely crush cookies. Place in a medium bowl, add butter, and mix well. Press mixture into bottom of a 9- x 13-inch baking dish; chill until ready to use.
Step 2
In a medium bowl, beat cream cheese, vanilla, and confectioners' sugar until smooth. Stir in 2 cups whipped topping. Lightly spread mixture evenly over cookie crust.
Step 3
In a large bowl, whisk together chocolate pudding and milk until thick. Evenly spread over cream cheese layer. Refrigerate 10 to 15 minutes, or until pudding is set.
Step 4
Spread remaining whipped topping over pudding layer and sprinkle with chocolate chips. Refrigerate 4 to 6 hours, or until set.