2 (3.4 ounce) boxes instant chocolate pudding

2 cups milk

1 (8 ounce) package cream cheese (softened)

1 (14 ounce) can sweetened condensed milk

40 Oreo cookies (divided)

1 cup chocolate milk

1 (8 ounce) package Cool Whip (divided)

Whisk together pudding and milk until pudding begins to thicken and set aside.
In a bowl, beat cream cheese until smooth. Slowly add in sweetened condensed milk and continue mixing until smooth.
Once mixed, fold in chocolate pudding and 1/2 the Cool Whip. Set chocolate mixture aside.
Dip Oreos one at a time briefly in chocolate milk and line them in a 9 x 9 inch dish (should be about 4 x 4 rows).
Top Oreos with chocolate pudding mixture and spread evenly.
Layer with 16 more chocolate milk dipped Oreos.
Top Oreos with remaining cool whip and crumble 8 extra Oreos over the top.
Place in the fridge for 2-4 hours to let Oreos soften.
Serve cold!