In a large mixing bowl, beat the cream cheese with a hand mixer until smooth.
Add the sour cream and beat for another minute or two until well combined.
In a separate small mixing bowl, combine the milk and pudding mix as directed on the pudding box. I find that a wire whisk works best for this. To avoid lumps make sure to add small amounts of mix at a time to the milk and whisk thoroughly before adding more.
Place the cookies into a large ziptop bag. Make sure to remove as much air as possible before you close it. You can use a rolling pin or some other blunt object to smash them, but I find that my hands are usually enough to crush them. You don't need uniform pieces unless you really want them. If you leave the pudding mixture on the counter while you do this, it should set up by the time you are finished.
Fold the pudding mixture into the cream cheese mixture. Keep as much air in the mixture as you can! This is what gives trifles their signature fluffiness.
Fold in the chocolate whipped topping, reserving about 4 ounces for garnish. The recipe originally called for 12 ounces in total, but they no longer sell that size and I find that I can always use the extra somehow! Again, keep as much air in the mixture as you can.
Now you're ready to begin layering the trifle. I highly recommend a trifle bowl if you have one, but if not, any large serving bowl with high sides will work. Clear glass or plastic is always best so that people can see your layers, however uneven they might turn out! If your bowl is wider at the top than the bottom, your layers may not be perfect. Don't let this stop you; the taste will still be wonderful.
Start with half of the cream cheese mixture. Make sure that the layer is as even as possible for best visual results. Try to keep smears up the side of the bowl to a minimum. This is the only tricky part and only matters if you're really trying hard to impress!
Next, layer half of the crushed cookie crumbs over the top of the cream cheese layer. This can look a little sparse but don't worry. You don't need a full "crust" for this to work, it's just a flavor and texture accent for the rest of the dish.
Finally, add one can of pie filling on top of the cookie layer. Do your best to spread this out evenly. Again, if you're trying to impress, be very careful of smears up the side of the bowl.
Repeat this process with the remaining ingredients. You may use the remaining whipped topping and/or chocolate sprinkles to garnish if you like, but if not, then you're done!
Cover tightly and chill until ready to serve. I find that the trifle sets up a little better and tastes best when it's cold, so the longer you can chill it before serving, the better. You can serve it immediately if you're in a hurry with no ill effects, so I haven't listed mandatory "cooking" or chilling time for this recipe. Use your best judgment.
