Make the Chocolate Cake:
- Preheat oven to 350°. Line two baking trays with parchment paper.
- Whisk together the flour, cocoa powder, baking powder, baking soda and salt. Set aside.
- In the bowl of a stand mixer, beat shortening and sugar on medium-high using the paddle attachment. Beat until pale and fluffy, about 3 minutes. Scrape down bowl.
- With the mixer on low, add egg and vanilla. Mix to combine.
- Slowly add the flour mixture, alternating with milk, until blended.
- Using a cookie scoop, drop onto baking sheets. Then using a toothpick or butter knife to gently create points on either side of the circle, creating the shape of a football.
- Bake 10 to 12 minutes, or until firm. Cool on racks then fill with filling, below.
Make the Cream Cheese Filling:
- With an electric mixer on medium high speed, beat butter and cream cheese until fluffy, 2 to 3 minutes.
- Reduce speed to low. Add sugar 1 cup at a time, and then vanilla, mixing until smooth and combined, scraping down sides of bowl as needed.
Assemble the Whoopie Pies:
- Fill a piping bag fitting with a star tip with your cream cheese frosting.
- Flip one of your Chocolate Whoopie Pies over so the bottom is facing up. Starting from the perimeter, frost your whoopie pie, working your way in, until the entire circumference is frosted.
- Gently press the bottom side of another whoopie pie on top, creating a “sandwich”.
- Use the remaining cream cheese frosting to pipe football laces onto the top of each whoopie pie.