Cookies and Cream cupcakes - part two!

I am afraid I am a bit of a perfectionist.

If I am not happy with the way something turns out, it haunts me until I can figure out what to do to make it right. Now, I try not to be like my grandmother about these things - she would serve dinner and then proceed to tell you that really, it wasn't very good and then list exactly why the dinner didn't measure up. I am learning to keep my opinions to myself. Plus, most of the time no one is going to notice anyway. They're just happy that you made something for them to eat! I know that's how I approach the dinner table.

My first cupcake recipe was also for cookies and cream cupcakes, but I was definitely not thrilled with the results. I thought the cookie on the bottom was soggy, and not crunchy like I wanted. The chunks on the top made it hard to fill the cupcakes. The frosting was grey, and gritty with the crumbs. The cookie shoved into the top looked like an after thought (or a tombstone). Plus, you can see a sausage grinder in the background of the photo. That's just silly.

Still, it was my first time, and you know, people really liked them, and they did taste good. They just didn't reflect what was in my head - a cupcake that really encompassed the cookieness and creaminess of the idea.

Soggy bottom being out, I borrowed from my key lime pie and s'mores cupcakes and did a baked cookie-crumb bottom that I topped with more chocolate, just because. I like this technique because I like the texture contrast. It doesn't show well in the photo (dark on dark), but it's definitely there and I think it adds to the cupcake.

I wanted the cake itself to be like the classic sandwich cookie: dark and not too sweet with that creamy filling (but without the marshmallow I had used before). I found a few Oreo knockoff recipes on the web and piecemealed my own together - sweet and yes, with shortening (that was necessary for color and texture and leave it out if you just can't bring yourself to do it. I think shortening has its place, myself. Like in piecrust. Anyways...), and thicker than my cupcake fillings usually are.

For the frosting, I really wanted to reflect that cream aspect, and after much thought, went with a whipped buttercream. The amount of air you beat into the butter makes it creamy and light like a whipped cream, but with much greater stability, and the frosting ends up tasting like melted vanilla ice cream. Crumbled cookies were the garnish and look pretty against the pale frosting.

These were the cupcakes for my son's third birthday - and everyone in attendance loved them. Liam himself just ate off the frosting with a spoon, took the lid off of the filling, and licked out that part, leaving the cake behind. Still not too shabby for a three-year-old.

This makes about 21 cupcakes.

~Chocolate Cupcakes~
For cookie bottoms:
1 1/4 cup chocolate cookie crumbs (about 2/3 of a package of chocolate wafers)
1/2 cup melted butter
1/2 cup chopped bittersweet chocolate

4 ounces bittersweet chocolate, chopped
1 cup dark cocoa powder
1 cup hot coffee
1 cup all purpose flour
1 cup sugar
1/2 tsp. baking soda
1/2 tsp. salt
2 tablespoons balsamic vinegar
6 tablespoons vegetable oil
2 eggs
1 teaspoon vanilla

Preheat the oven to 350 degrees.

Line 21 standard-sized muffin cups with baking liners.

Combine together the chocolate cookie crumbs and melted butter until the mixture is damp and crumbly but holds together when squeezed into a ball. Place about a tablespoon of the crumb mixture into the bottom of each muffin cup, dividing as evenly as possible among the 21. Press down gently with your fingers to cover the bottoms in an even layer. Sprinkle over with the chopped chocolate. Bake for 8 - 10 minutes or until the chocolate melts a bit. Let cool for 10 minutes before filling with the cupcake batter.

Combine the chocolate and cocoa in a medium mixing bowl and pour hot coffee over. Let sit until chocolate is melted. Stir to combine; set aside.
In a large mixing bowl, combine flour, sugar, baking soda, and salt. To chocolate mixture add vinegar, oil, eggs, and vanilla; mix well with fork to combine. Pour over flour mixture and stir well.

Pour the batter into the lined muffin tin (filling about 3/4 full). Bake at 350 for 15 - 18 minutes or until a toothpick inserted comes out clean. Let cool for about 10 minutes in pan and then cool completely on a wire rack.

~Vanilla filling~
1/2 cup unsalted butter, room temperature
1/4 cup vegetable shortening
1/2 teaspoon salt
3 cups powdered sugar
2 tablespoons cream or milk
1 teaspoon vanilla (or 1/2 teaspoon vanilla bean paste or 1/2 teaspoon ground vanilla bean)

Mix together the butter and shortening in the bowl of an electric mixer until fully combined. Slowly add in the powdered sugar, salt, and vanilla. Add in the cream or milk as needed to achieve the proper consistency (you're going for the filling of an Oreo cookie, remember, but just a little creamier than that).

Once the cupcakes have cooled, cut out a cone-shaped portion out of the top of each cake. Slice off the excess cake from the cone (leaving the flat cap) and reserve the top. Fill the resulting hole with about a tablespoon of the marshmallow filling (or however much you need). Replace the cap. Repeat with the remaining cupcakes, and then put in the refrigerator for about 15 minutes to chill and set the filling (once cool, it will become very thick and hold the caps in place).
 
~ Whipped vanilla buttercream frosting ~ 

3 sticks unsalted butter, softened
3 cups powdered sugar
3 tablespoons
1/2 teaspoon salt
1 teaspoon vanilla extract
Crumbled Oreo cookies, for garnish

In your electric mixer, beat the butter using the paddle attachment for 8 minutes. No, I am not kidding.

Slowly add in the powdered sugar, beating in after each addition and scraping down the sides of the bowl, until combined.
Add in the rest of the ingredients and mix on low speed for 1 minute, then on medium speed for 6 minutes. Frosting will be very light, creamy, and fluffy.

Pipe on the frosting using a pastry bag or just swoop it onto the cupcakes with a spatula, and sprinkle the crumbled Oreos on top. Store in the refrigerator, but ideally let come up to room temperature before serving.