Cheesecake NOTE: You will need to prepare cheesecake at least 6 hours or overnight before you wish to assemble the cheesecake!
Preheat oven to 350F (175C) and line an 8" springform pan with parchment paper (I remove the bottom, cover with parchment paper and return the rim (parchment paper will be sticking out the sides). This helps to make the cheesecake more easily transferable to the center of the other cake.
With mixer on low-speed, beat together softened cream cheese, sugar and vanilla, scraping down the sides with a spatula occasionally to ensure ingredients are smooth, lump-free, and well-combined.
Add sour cream and stir until combined.
Add eggs, one at a time, beating until just mixed after each addition (and scraping down the sides after each addition).
Stir in Oreo pieces.
Pour cheesecake batter into prepared springform pan.
Bake on 350F (175C) for 40 minutes or until edges are set and cheesecake is just slightly jiggly in the center. Remove from oven and allow to cool to room temperature before transferring to fridge to cool for at least 6 hours. Do not remove from springform pan.
Cake Preheat oven to 350F (175C) and generously grease and flour two 8”-round cake pans.
In large bowl, whisk together flour, sugars, cocoa powder, baking soda and salt.
Add oil and stir well (mixture may be dry).
Add eggs and vanilla, stirring until combined.
With mixer on low-speed, gradually stir in buttermilk until batter is uniform.
Add hot coffee or water and stir until combined. Scrape down sides and bottom of bowl as needed.
Divide batter evenly between prepared pans.
Bake in center rack of 350F (175C) oven for 35 minutes or until toothpick inserted in center comes out mostly clean or with a few moist crumbs.
Allow cakes to cool in pans for 10-15 minutes then carefully invert onto a cooling rack to cool completely before assembling.
Frosting & Assembly Prepare frosting according to recipe instructions.
Once cake and cheesecake have both cooled completely, carefully transfer one chocolate cake round to cake stand/serving platter and layer the top with the a thin layer of frosting.
Run a knife around the inside edge of the springform pan to loosen the cheesecake and remove the sides of the pan. Carefully place the cheesecake on top of first chocolate cake layer and spread another thin layer of frosting over the cheesecake (if there is moisture/condensation on the cheesecake, simply pat dry with a paper towel before frosting).
Place second chocolate cake layer on top of cheesecake layer
Frost cake all over. If desired, use your hands to press cookie crumbs part-way up the sides of the cake and sprinkle over the top of the cake. If decorating cake with additional frosting on top, I recommend a large closed-star tip, like the Ateco 846 that I used in photos (linked in the "equipment" section).