Put butter in mixing bowl and whip at high speed for 4-5 minutes. Butter will turn a lighter shade.
On low speed, add powdered sugar, one cup at a time, until completely incorporated. Add the whipping cream in between to keep the mixture whipping smoothly.
Once the powdered sugar and whipping cream are incorporated into the butter, whip the mixture on high speed for another minute.
Pour crushed OREO cookies into frosting. If you plan to pipe the frosting onto the cupcakes, be sure to crush them with a food processor so the pieces don't clog the piping tool. Add vanilla and whip at high speed for another minute.
Pipe onto cupcakes and put a Carrot Cake OREO cookie on each cupcake.