Preheat the oven to 350 degrees F, line a cupcake pan with paper liners. Set aside.
In a large bowl add all the ingredients for the cupcakes and whisk together until combined. Set aside.
Place one Oreo in each one of the cupcake liners.
With a medium cookie scoop, scoop about 1½ scoops of batter and place on top of each Oreo. If you do not have a medium cookie scoop this is about 3 Tablespoons.
Place the cupcakes in the oven and bake for 20 to 22 minutes or until a cake tester comes out clean.
Remove the cupcakes from the oven then remove each one from the cupcake pan and transfer them to a wire rack to cool completely.
Meanwhile, beat together the heavy cream, powdered sugar, and pudding mix in a stand mixer fitted with the whisk attachment. You can also do this with an electric hand mixer as well.
Place frosting in a piping bag, cut the tip off so you have a larger hole and pipe a large mound onto the tops of the cupcakes.
Place the crushed Oreos in a small bowl and roll the tops of the frosted cupcakes in the crushed Oreos so they stick to the frosting.
Top with an Oreo and a piece of the cookies ‘n cream chocolate bar if desired for garnish.