Remove 8 Oreos from the package and place on a cutting board.

Cut the cookies into small, ¼” pieces, set aside.

Put the remaining Oreos into the container of a food processor fit with an “S” blade.

Process until the mixture resembles coarse crumbs. You may need to pause, break apart cookies that get stuck to the blades, and continue processing.

If you don’t have a food processor, you can crush the Oreos with a rolling pin.

Set aside.

In a medium bowl, whisk together milk and pudding. Set aside in the refrigerator to solidify.

In the bowl of your standing mixer or with a hand-held mixer in a large bowl, cream together butter and cream cheese. Beat until well combined & smooth (about 30-60 seconds).

Add powdered sugar and beat until smooth.

Add pudding to the butter/cream cheese mixture (make sure it has set before adding), and beat on low speed to combined.

Fold in cool whip until the mixture is homogenous (uniform throughout).

Layer the pudding mixture and cookies. Start by pouring 2 cups of pudding mixture into the bottom of a trifle dish and spread it until level.

Sprinkle ½ cup cookie crumbs and ¼ cup chopped cookies evenly over the pudding.

Repeat using 2 cups of pudding, ½ cup cookie crumbs and ¼ cup chopped cookies for each layer.

Add gummy worms to each layer as desired, or only add some to the top.