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For the cake:
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Preheat oven to 350u00b0F and spray three 9-inch round cake pans with nonstick baking spray. Set aside.
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In a large bowl, combine cake mix, eggs, butter, and milk until smooth. Divide between cake pans. Bake for 30-35 minutes or until a toothpick inserted in the center comes out clean. Cool completely.
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For the Oreo frosting:
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In a large bowl, beat butter and vanilla until light and fluffy. Add powdered sugar a little at at time. Add heavy cream as needed to reach desired consistency. Fold in crushed Oreos.
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Scoop 1 cup of frosting into a piping bag and set aside.
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For the chocolate ganache:
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Pour heavy whipping cream into a small saucepan. Heat over medium heat. Pour chocolate chips into a medium heat-safe bowl.
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Once heavy whipping cream starts to simmer, remove from heat and pour onto chocolate chips. Allow to sit for 1 minute before whisking until smooth. Pour into a squeeze bottle.
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Once the cakes are cooled, remove from pans. Using the cake leveler, cut domes off the tops of the cakes to even them out.
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Place one cake round onto the cake board. Scoop 1 cup of frosting onto the top of the cake round and spread evenly with an offset spatula. Repeat with remaining layers.
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Spread top and sides of cake with remaining frosting. Refrigerate for at least 1 hour.
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To decorate, remove cake from fridge and drip ganache all around the edge of the cake. Pipe dollops of frosting onto the top of the cake using a star tip. Place whole Oreos onto the sides of the dollops.