Crush the Oreos into bite-sized pieces; set aside. Don't crush the Oreos too much, they make up quite a bit of volume in this trifle. A quick crush with a rolling pin will do the trick!
18.1 ounces Oreo cookies
In a large bowl, beat the cream cheese until smooth. Slowly add sugar and 1/4 cup of milk. Beat until creamy, then stir in 2 cups of the whipped topping and set aside. Reserve the remaining whipped topping for later use.
8 ounces cream cheese, 1/4 cup granulated sugar
In a large bowl, whisk together pudding mixes and remaining 4 cups of milk for 2 minutes.
7.8 ounces instant chocolate pudding
To Assemble
Layer 3/4 cup of Oreos into the trifle bowl. Top with 3/4 cup of pudding followed by 1/2 of the cream cheese mixture.
Repeat the layers above.
Finish with the last of the Oreos and the remaining pudding. Lastly, top with 8 ounces of whipped topping and any optional garnishings you'd like!
The pudding layer should be thick, not runny, so that it sits between the layers well and doesn't seep down the bowl.
Let your cream cheese soften at room temperature before beginning so your mixture isn't lumpy. I cut mine into cubes and let it rest on the counter for 30 minutes or so to help speed up the process.