Make chocolate cupcakes batter, either homemade or from a cake mix. Line a muffin pan with cupcake liners and spray lightly with cooking spray.
Add a whole Oreo cookie to the bottom of each liner, and spoon cupcake batter over top.
Bakecupcakes at 350 degrees for 17-24 minutes, or until a toothpick inserted in the center comes out clean.
For the Frosting:
Make Oreo Frosting: Mix the butter with electric beaters until light and fluffy, about 3 minutes. Add powdered sugar, cream and vanilla and mix well, until light and fluffy. Stir in crushed Oreos cookie crumbs.
Frost cupcakes, once cooled completely. Add an Oreo on top, if desired.
Video
Notes
Make Ahead Instructions: Unfrosted chocolate cupcakes will keep, covered, at room temperature or in the fridge for 2-3 days. Oreo frosting will keep in the fridge for 1-2 weeks. Freezing Instructions: I recommend storing the frosting and cupcakes seperatly, in air-tight containers in the freeze for up to 3 months. Allow frosting to thaw completely at room temperature before frosting cupcakes. To freeze frosted cupcakes, flash-freeze them uncovered on a tray for 30 minutes (to help the frosting keep its shape) before placing them in a freezer safe container.