Preheat oven to 350 degrees. Spray a 13x9 inch baking dish with cooking spray and set aside.
In a large bowl, stir together the cake mix, eggs, water, and vegetable oil until moistened, then beat with an electric mixer on medium speed for two minutes. Pour the batter into the prepared baking dish.
Bake in the preheated oven for 30-35 minutes until a toothpick inserted in the center comes out clean.
Remove cake from the oven and place on a wire rack to cool completely.
In a medium mixing bowl, combine the chocolate pudding mix and milk. Stir for two minutes, until smooth and thickened.
After cake is completely cool, use the round handle of a wooden spoon to poke holes all over the surface of the cake. Spread the chocolate pudding over the top of the cake, making sure to push it down into the holes.
Next, spread the cherry pie filling over the top of the pudding layer, followed by the thawed whipped cream. Cover the cake and place in the refrigerator to chill for at least 1 hour.
Right before serving, decorate the top of the cake with fresh cherries and the chopped chocolate, if desired. Serve and enjoy!