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Cut the cold butter into pieces, about 1 tablespoon in size. Using the paddle attachment, whip the butter at medium high speed for 3-4 minutes, scraping down the bowl occasionally. Beat the butter until it looks lighter in color.
Slowly add the powdered sugar, 2 cups at a time, adding the heavy whipping cream intermittently, mixing on low speed until it’s incorporated into the butter. Then increase the speed to high and beat for 30-60 seconds. Repeat until all your powdered sugar has been added.
In a food processor, grind the Oreos into a fine crumb. Add the crushed Oreos to the frosting along with the vanilla extract. Slowly beat the crumbs into the frosting then beat at a high speed for 60 seconds.
In a large piping bag fitted with a large closed star tip, pipe the frosting onto the cupcakes and place an Oreo in the side.