Adjust the oven rack to the 2nd level mark (just above center) and preheat the oven to 375º F.
On a well-floured, clean surface, roll out one of the discs of pie dough you made earlier (or unroll if using store-bought) ) and carefully place into the 2, 9″ pie plates. Trim and crimp the edges to your liking, then place it back in the refrigerator as you make the cake and chocolate layers.
For the top cake layer: In a medium bowl, whisk together the all-purpose flour and baking powder. Set dry mixture aside.
Using a hand mixer or stand mixer fitted with a paddle attachment on medium-high speed, cream the granulated sugar and vegetable shortening together until blended. Add in the eggs and vanilla extract, and mix until combined.
Reduce the mixer speed to low and alternate between adding the dry mixture and milk. Mix together until just combined, then set aside.
For the bottom chocolate layer: In a medium bowl, whisk together the granulated sugar and unsweetened cocoa powder.
Slowly pour in the boiling water and add in the vanilla extract. Stir continuously until unsweetened cocoa powder is fully dissolved.
Divide and pour the cake batter into the 2 unbaked 9" pie crusts, then divide and pour the chocolate layer over top of each. The chocolate layer sinks to the bottom during baking which then forms the thick chocolatey layer on the bottom. It also gives the top of your funny cake a nice chocolate swirl on top!
Place the funny cakes in the oven side-by-side and bake for 45-50 minutes or until a toothpick inserted in the center of the cakes comes out clean. Mine baked for almost the full 50 minutes. I highly recommend using a x-large baking sheet or jelly roll pan to move the funny cakes into the oven and removing when done. It makes it a lot easier!
Remove from oven and allow to cool completely before serving.