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Pulse Oreos into fine crumbs and mix with melted butter. Press into a 9x13-inch pan and refrigerate.
Beat cream cheese and peanut butter until smooth. Add powdered sugar and mix well. Fold in Cool Whip and spread over crust. Top with chopped peanut butter cups. Chill.
Whisk pudding mix and milk. Let set for 5 minutes, then spread over peanut butter layer.
Top with Cool Whip and remaining peanut butter cups. Cover and refrigerate at least 2 hours before serving.