Using a mixer, mix up your cream cheese and Cool Whip first, then add in your pudding and milk.
Crush 1 package of Oreos at the bottom of your bowl...or in my case I crushed a layer at the bottom, added some pudding, added some more crushed oreos, then more pudding, then topped it off with the rest of the oreos.
If you have a large bowl you can determine the order of the oreo to pudding ratio.