Preheat oven to 325°F. Prepare Classy Chocolate Pound Cake Mix according to package directions using water and butter. Place a small amount of cake batter in the bottom of a cupcake liner. Place a tablespoon of cherry pie filling in the middle of the batter. Top with remaining cake mix batter.
In large mixing bowl, combine thawed whipped topping, softened cream cheese and sugar. Mix until light and fluffy. Place in a piping bag.
Once cupcakes have cooled, pipe cream filling on top. Top with a small amount of cherry pie filling in the middle of the cupcake. Garnish with some chocolate.