Grease 24 cupcake compartments in 2 (or 4 depending on your size pans) cupcake pans. I don’t use cupcake liners so that you can see the beautiful crust on these babies!
In a food processor (or however you like to crush things) crush about 24 Oreo cookies until you have 2 cups of finely crushed Oreo crumbs. Mix the Oreo crumbs with the 5 Tbsp of melted butter until completely combined.
Measure about a tbsp of cookie crust into cupcake pans filling 24 cupcake holes.
Make the brownie mix according to the box. Mix in 3/4 cup of broken (not crushed to dust!) Oreo cookies into the brownie batter.
Evenly distribute the brownie batter (about a heaping tbsp in each cup) over the cookie crust in all 24 cupcake cups.
Bake at 350 degrees for 22 minutes or until a toothpick comes out almost clean or you can see that the brownies are set.
Let cool for 10 minutes before carefully removing from pans. Cool cupcakes completely.
Make the Frosting
In the clean bowl of an electric mixer fitted with the whisk attachment, combine the whipping cream, powdered sugar, and vanilla extract. Beat on medium-high speed until the whipped cream holds stiff peaks. Gently fold in the cookie crumbs with a spatula.
Put frosting into a pastry bag with a large round tip and frost the cupcakes to your liking. I used Wilton Tip #12 but you could you frost the cupcakes however you like.
Stick a Oreo half in the frosting of each cupcake for a little pizzazz. That’s it. Enjoy. With the whipped cream type frosting, I stored my cupcakes in the refrigerator.
I suggest storing the cupcakes in the refrigerator.