In a mixing bowl, beat the softened cream cheese with an electric mixer until smooth and creamy.
Gradually add the powdered sugar and vanilla extract to the cream cheese, mixing until well combined.
Gently fold in the whipped topping until fully incorporated, being careful not to deflate the mixture.
In a separate bowl, combine the graham cracker crumbs and melted butter. Mix until the crumbs are evenly coated and resemble wet sand.
In serving dishes or cups, layer the graham cracker mixture at the bottom.
Spoon a generous amount of the cheesecake fluff on top of the graham cracker layer.
Add a layer of cherry pie filling over the cheesecake fluff.
Repeat the layers until the cups are filled, ending with a layer of cherry pie filling.
Optionally, sprinkle chopped walnuts or pecans on top for added crunch.
Chill in the refrigerator for at least 30 minutes before serving for the best flavor and texture.