Preheat oven to 350 degrees F (175 degrees C). Lightly spray bottom and sides of a 9x13-inch baking pan with cooking spray.
Stir cookie mix, oil, and egg together in a large bowl until a soft dough forms. Drop 3 heaping tablespoons of dough on an ungreased baking sheet 2 inches apart to make 3 cookies.
Bake cookies in the preheated oven until set, 12 to 13 minutes. Cool on the baking sheet, 2 minutes. Transfer to a wire rack to cool completely, about 15 minutes.
Press remaining dough evenly into the bottom of the baking pan.
Measure 1 cup cherry pie filling into a small bowl and reserve for the topping; cover with plastic wrap and store in the refrigerator.
Beat cream cheese, remaining cherry pie filling, and white sugar together in a large bowl with an electric mixer on medium speed until well-blended, about 2 minutes. Spread cream cheese mixture over dough.
Bake in the preheated oven until set, 35 to 40 minutes. Let cool, about 30 minutes. Refrigerate until chilled, about 1 hour.
Spread whipped topping over cream cheese layer. Top with spoonfuls of the reserved pie filling. Crumble cookies into coarse crumbs and sprinkle on top. Chill until flavors blend, at least 1 hour. Cut into 20 bars.