In the bowl of an electric mixer, using the paddle attachment, cream together the softened cream cheese and butter until smooth.
Add in the powdered sugar and vanilla; continue to mix until combined and smooth.
Switch out the paddle attachment for the whisk attachment, if you have one, and add in the pudding mix, followed by the milk; mix per instructions on the instant pudding box; usually around 2 minutes.
Allow the pudding/cream cheese mixture to set until just firm; since the recipe uses instant pudding mix, this takes about 5 minutes..
Finally, fold in the container of Cool Whip.
Add the cheesecake pudding mixture to the top of the crumb mixture.
Set the jars in the refrigerator and allow to chill for up to 2 hours.
Remove from the refrigerator and add the cherry pie filling.