Prepare the pudding according to directions on the box and, using a spatula, gently fold in the thawed cool whip. Fold together until smooth.
Fill up the plastic cups with the pudding mixture. RIGHT before serving (to avoid soggy cookie crumbs), top with the crushed cookies (I just put the cookies in my blender and pulse them until they are in fine crumbs; no need to remove the filling!)
On the milano cookies, use the edible food gel to write "RIP" on each one.
Right before serving, add the milano cookies to the pudding cups (they get soggy if added in advance). If desired, add in a gummy worm on top.