Oreo Cupcakes

My boyfriend is not a big dessert fan. (How we ever ended up together with such widely differing views on dessert, I'll never know, but somehow we make it work.) He rarely eats sweets, and never after 9PM. There is only one exception to this...if there are Oreos anywhere in sight, all rules are out the window. So when determining what to bake him for his birthday, I knew it had to have Oreos in it. And since I like cupcakes, it was an easy decision. The hard part was coming up with right combination of cake and frosting that best represented the cookies and cream flavor I was looking for. I wanted a dark, dense, semi-sweet chocolate cake, and a light, airy frosting. Here's what I came up with:

Oreo Cupcakes

Cake Ingredients:
2 cups boiling water
1 cup unsweetened cocoa powder 
2¾ cups flour
2 tsps. baking soda
½ teaspoon baking powder
½ tsp. salt
1 cup butter, softened
1½ cups sugar
4 eggs
1½ tsps. vanilla extract
24 Oreo cookies, plus more for garnish if desired

Cake Directions:
Preheat oven to 350 F. Line cupcake pans with paper liners. Carefully separate cookies so that one side has the cream intact and only the cookie remains on the other side. Set aside the cookies without the cream, to be used later in the frosting. Place the cookie halves with the cream, cream side up, at the bottom of each paper liner. In a medium bowl, pour boiling water over cocoa and whisk until smooth. Let mixture cool. Sift together flour, baking soda, baking powder and salt; set aside. 
In a large bowl, cream butter and sugar together until light and fluffy. Beat in eggs one at a time, then beat in vanilla. Add the flour mixture alternately with the cocoa mixture, beginning and ending with the flour mixture. Beat just until mixed. Fill paper liners ¾ full. Bake for 21-24 minutes, or until toothpick inserted into center comes out clean. Cool in pans 5-10 minutes or until safe to touch before removing. Place in refrigerator until completely cooled and ready to frost.

Frosting Ingredients:
4 cups (2 pints) heavy whipping cream
½ cup powdered sugar
1 tsp. vanilla extract
24 Oreo cookie halves

Frosting Directions:
In a food processor or blender, process cookie halves until blended into fine crumbs. In a large bowl, combine the whipping cream, powdered sugar and vanilla extract. Beat on medium-high speed until the whipped cream holds stiff peaks. Gently fold in the cookie crumbs with a spatula. Scoop mixture into pastry bag and pipe onto cupcakes. Garnish with Oreo cookies if desired.

The final results were better than I had even dared to hope. The cake was everything I wanted: dark, dense, rich. The frosting is the literal interpretation of the cookies and cream taste I wanted, without the heaviness of a standard buttercream frosting. And it's delicious. I could eat it straight out of the bowl. The only thing I had qualms about was the cookie at the bottom of the cupcake. It didn't soften up during the baking process like I hoped it would, so the crisp texture of the cookie with the softness of the cake was quite the juxtaposition. But it's growing on me. I'll probably do it the same way when I bake them again. And I will bake them again, for sure.

Sources: Ingredients and proportions have been changed, but the main inspiration came from these two recipes- http://allrecipes.com/recipe/dark-chocolate-cake-i/detail.aspx, http://buddingbaketress.blogspot.com/2011/03/oreo-cupcakes.html