Mix the cake batter as directed on box. Make the cake with two cake pans or 24 cupcakes. If making cake, divide up the batter equally between the two pans you will be using. Once baked, let the cakes cool completely.
With a handheld or stand mixer fitted with a paddle attachment, beat the butter on medium speed until creamy, about 2 minutes. Add 4 and 1/2 cups confectioners’ sugar, heavy cream, and vanilla extract. Beat on low speed for 30 seconds, then increase to high speed and beat for 3 full minutes. Add up to 1/2 cup more confectioners’ sugar if frosting is too thin or another tablespoon of cream if frosting is too thick.
Crush up 3/4 of the package of Oreos. I put the Oreos inside a large plastic Ziploc bag and used a rolling pin to crush them up. You can use a food processor as well.
Add the crushed Oreos to the frosting and beat on low speed to incorporate the Oreos.
Remove the cakes from the pans.
Place 1 cake layer on your cake stand, cake turntable, or serving plate. Spread frosting evenly on top. Use your own judgement on how much to use.
Top with 2nd cake layer and evenly cover the top with frosting. Cover the sides of the cake with frosting. Use a bench scraper or a butter knife to smooth out the frosting on the sides of the cake.
Using a flower tip and a piping bag pipe frosting around the top of the cake. Sprinkle the top with crushed Oreos. Cut a few of the remaining Oreos in half and place on top.