Prepare the Pudding Mixture
In a large bowl, whisk together pudding mix and cold milk for about 5 minutes until soft-set.
Fold in whipped topping gently. Set aside.
Make the Cream Cheese Layer
In another bowl, beat cream cheese and butter until smooth and creamy (about 30 seconds).
Add powdered sugar, mix on low, then beat on high until smooth.
Add pudding mixture and beat until fully combined. Chill until ready to use.
Prepare Oreo Crumbs
Crush Oreos (with filling) into fine crumbs using a food processor or by hand in a sealed bag.
Assemble the Layers
Spread 1/3 of the pudding mixture into the bottom of a trifle dish.
Add 1/3 of the crushed Oreos and spread evenly.
Repeat layers two more times, ending with Oreo crumbs on top.
Chill and Serve
Cover and refrigerate for at least 12 hours.
Garnish with gummy worms or decorations before serving.
Chilling overnight enhances flavor and texture.
Use a clear dish to showcase layers.
Do not skip the resting time for best consistency.