Super Bowl Coffee Whoopie Pies

For last year's Super Bowl, I may have gone slightly overboard by making a dish for each team (see Denver's Double Cheddar Beer Bread and Seattle's White Mocha Caramel Frappuccino Cupcakes), so this year I decided to consolidate my baking into one mega-cookie encompassing both teams with the New England staple whoopie pie featuring a coffee cream cheese filling in honor of the land of Starbucks.

Coffee Whoopie Pies
Adapted from this post, Mrs. Fields, and Food Network
Time: 60 minutes (plus cooling)
Servings: 6 giant whoopie pies

Properly mixed batter

Cookies
2 1/2 cups all-purpose flour
1 tsp baking soda
1/4 tsp salt
1 tbsp ground espresso
1/2 cup unsweetened cocoa powder
1 cup dark brown sugar, packed
3/4 cup white sugar
1 cup salted butter, softened
3 large eggs, room temp
1 tbsp pure vanilla extract
2 cups semisweet chocolate chips

Sugar and butter made better with caffeine!

Filling
8 oz cream cheese, softened
1 1/2 sticks unsalted butter, softened
1/4 tsp fine sea salt
2 cups powdered sugar
3-5 tbsp freshly brewed espresso (I used Cafe Bustelo)

1. Preheat the oven to 300 F.
2. Whisk the flour, baking soda, salt, ground espresso, and cocoa powder together in a large bowl. Set aside.
3. Cream the butter and sugars together in a stand mixer until they form a grainy paste.
4. Mix in the vanilla and one egg at a time until fully incorporated. 
5. Add the flour mixture to the wet mixture in several batches. Be careful not to overmix.
6. Stir in the chocolate chips.
7. Scoop ~ an ice cream scoop's worth of batter onto a baking sheet lined with a silicone baking sheet. This is key to get the right cookie height and texture.
8. Bake for 18-22 minutes, rotating once halfway through. When the edges start to firm up, they are done.
9. Let cool on the baking sheets for an additional 3 minutes. Then transfer to wire racks to finish.
10. Make the filling by creaming the butter, salt and cream cheese together until smooth using an electric mixer with a whisk attachment. Make sure the cream cheese and butter are near room temp or you'll get nasty lumps.
11. Mix in the powdered sugar 1 cup at a time. 2 cups gives a good level of sweetness that isn't overwhelming, but feel free to adjust.
12. Add in the brewed espresso 1 tbsp at a time until you reach the desired level of amazing coffee flavor. 
13. Once the cookies have cooled, assemble the whoopie pies by scooping frosting in between two giant cookies.
14. Let cool in the fridge until ready to serve (at least 1 hour).

They already look so perfect and they're not even sandwiched around frosting yet!

Whoopie pies may just be my favorite dessert, and this was the closest I have come to recreating the SusieCakes awesomeness that introduced me to them. Using a silicone baking sheet produced the best cookie quality yet, as the cookies spread less and maintained their jaw-unhinging height better than ever before (it's also important not to overmix or you'll get a batter that's far too thin). The coffee flavor did not really come through in the cookie (thanks to all the awesome chocolate), but the frosting more than made up for it, as the coffee alterations led to the best whoopie pie filling I have made yet.

This juggernaut of a cookie sandwich casts a large shadow over all other baked goods

Now enjoy a special addendum on an alternate version of the cookie that I made during one of my Robin Night Shift care packages.

The Radioactive Cherry Almond Cookie Option

I was worried they were going to jump up and attack me.

Additional Ingredients (cookie only)

Maraschino cherries, drained and cut in half

Almond slivers

Switch in dark chocolate cocoa powder 

This cookie previously appeared in the toxic waste scene at the end of Robocop.

1. Go to the store hoping to get fresh cherries for some amazing cookies. Realize it's winter, and there are no fresh cherries available, so settle for super sweet, bright red maraschino cherries.
2. Follow the above recipe for making the cookies but substitute in the dark chocolate cocoa powder, and stir in the cherries and almonds at the end.
3. Be amazed that something that looks like a melting alien can taste so good!

Success! One of them looked normal and edible!

Despite their odd, radioactive appearance, these cookies were actually pretty tasty. I was hoping to recreate the amazingness of these Dark Chocolate Cherry Almond Muffins in unhealthier seeming cookie form, and for the most part I succeeded. This definitely will require some revisiting with fresh cherries at a later day to achieve maximum cookie excellence.