Remove pie crust top from pie. Place in food processor with butter and sugar. Pulse until pie crust breaks up, it might form a ball and that's okay. On a baking sheet lined with parchment paper (or a silicone mat like pictured) lay out little dollops of the pie crust mixture. Place in the oven for 10 minutes or until crust turns a golden brown. Take out of the oven and let cool completely.
Scoop out cherry pie filling and place in food processor (or blender) and blend until smooth. Place in a medium bowl and add the Cool Whip. Gently fold the two together until combined.
Pipe into glasses and top with pie crust crumbles. Add a dollop of Cool Whip and more crumbs for garnish, if desired. Serve and enjoy!