1 cup store-bought whipped topping, such as Cool Whip, frozen
2 1/3 cups all-purpose flour
2 ounces semisweet chocolate, finely chopped
1 cup dark cocoa powder
2 teaspoons baking powder
1 teaspoon baking soda
1 teaspoon kosher salt
3 large eggs
2 cups granulated sugar
1 1/4 cups whole milk
1 cup vegetable oil
1 tablespoon vanilla extract
2 teaspoons instant espresso powder
30 to 40 Sweet Tart bone-shaped candies, or similar
10 to 16 gelatin candy pumpkins
Preheat oven to 350 degrees. Place oven rack in the center. Butter and flour a 9 x 13-inch cake pan.
To make the dirt: In the bowl of a food processor fitted with the blade attachment, process 6 Oreo cookies until they resemble wet dirt. Set aside.
To make the cookie cream: In the bowl of a food processor, add the remaining 10 Oreo cookies and pulse until finely chopped. Set aside.
Pour the heavy cream into a large mixing bowl. Using a hand mixer, whip the cream to soft peaks. Add the whipped topping and beat to stiff peaks. Add the 10 processed cookies, and fold into the cream. Pour the cream into a large pastry bag. Place in refrigerator until ready to use.
To prepare the dry mixture: In a medium mixing bowl, whisk all dry ingredients until combined. Set aside.
To prepare the wet mixture: In a large mixing bowl, add the eggs and sugar. Using a hand mixer, beat until light and fluffy. Add the milk and vegetable oil. Beat again until well combined. Add the vanilla extract and espresso powder. Beat again. Add the dry ingredients in 2 additions, beating after each until just incorporated.
Pour the batter into the prepared pan. Bake for 40 to 45 minutes until a skewer inserted into the middle of the cake comes out clean. Cool for 20 minutes.
To assemble the cake pops: Assemble the cake pop molds according to package instructions.
Insert the open end of the mold into the cake and twist before pulling out. Cake will partially fill the mold. Using a spoon, press the cake to the bottom of the mold. Insert 1 to 2 of the candy bones, making sure they are visible from the outside. Repeat this process with 9 more of the cake pop molds.
Pipe about 1 inch of the cookie cream on top of each cake. Scoop the remaining cake into the tops of each cake pop to almost fill. Pipe a dollop of cream on top. Sprinkle with cookie dirt, and finish with a candy bone and pumpkin on top.