My old favorite cupcake and favorite frosting must now move aside. These cupcakes blow just about every other dessert out of the water. They start with a rich, but not overly fudge-like, chocolate cupcake. Then, you scoop out the centers and fill it with actual homemade Oreo filling. Then, you top it with an Oreo whipped cream frosting that can best be described as a light cheesecake being piped on top of the cupcakes.
One would think that these would be hard to make. I know I did. But not only are these cupcakes ridiculously tasty, the are also ridiculously easy. You don’t need an electric mixer for the cupcakes (you do need one for the filling and the frosting). The filling can be made in 5 minutes. And the frosting is simple, not to rich, and is, in my opinion, the best part of the whole cupcake.
Time, active: 30 minutes. Time, inactive: 30 minutes. Total time: 1 hour.
Servings: 12 standard cupcakes
Ingredients for the Cupcakes
1 cup all-purpose flour
1 cup white sugar
1/2 cup unsweetened cocoa powder
1 teaspoon baking powder
1/2 teaspoon baking soda
1/2 cup whole milk
1/4 cup vegetable or canola oil
1/2 teaspoon vanilla extract
1/2 cup boiling water
To Make the Cupcakes
Preheat oven to 325 degrees fahrenheit. Line a standard cupcake pan with liners. Set aside.
Throughly whisk all the dry ingredients together in a large bowl.
Add the wet ingredients, then whisk until completely combined.
Divide batter evenly between each holder, ideally filling each one around 3/4 of the way.
Bake for 15 minutes, or until a toothpick inserted into the center comes out clean.
Remove from oven, let cool in the pan for 5 minutes, then remove and place on a wire cooling rack until completely cool before going to the next step.
Ingredients for the Filling
1/4 cup (4 tablespoons) salted butter, softened, but with no melted spots
1/4 cup vegetable shortening
2 cups powdered sugar
2 tablespoons whole milk
1 teaspoon vanilla extract
To Make the Filling
In an electric hand or stand mixer, cream the butter and shortening until whipped and creamy in appearance.
Beat in the powdered sugar and the milk, scraping down the bowl after every addition.
Add in the vanilla.
With a knife, cut out a small cone from the center of each cupcake (see the picture of the cut in half cupcake above). Now, scoop the filling into a pastry bag, cut off the tip, and pipe filling into the holes.
Ingredients for the Frosting
8 ounces of cream cheese
1/2 cup of white sugar
1 teaspoon vanilla extract
2 cups of heavy whipping cream
10 Oreo cookies, blended into a medium-grain powder. I prefer a blender for this step. (you leave the cream centers in)
To Make the Frosting
In an electric hand or stand mixer, cream the cream cheese and sugar together until whipped and creamy in appearance. Gradually add the heavy whipping cream. Add the vanilla extract. Scrape down the sides of the bowl and whip on high speed until stiff peaks form (To tell if there are stiff peaks, drag a spoon or your finger through it. Gently flip the spoon to where it’s upside down, then right side up again. If it holds it’s shape, it has stiff peaks). Now, switch to low speed and fold in the ground Oreos.
Pipe onto cupcakes as desired and garnish with an Oreo.
Store the finished cupcakes in the refrigerator for up to 1 week.
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