Preheat an oven to 180c (350f) and prepare 3 8-inch baking pans with parchment paper.
Into a big mixing bowl, add the soft butter, and sugar. Mix with an electric hand mixer until creamy and smooth for about 3 minutes.
Add the vanilla extract, vinegar, vegetable oil, sour cream, and kosher salt, and mix until creamy.
Add the eggs one at a time mixing constantly until a creamy mixture forms.
Then into a medium mixing bowl, add the flour, and baking powder. Mix with a whisk until combined.
Add ½ of the dry mixture and the milk and mix it until almost combined.
Add the other half of the dry ingredients, and the oreo chunks, and mix until just combined.
Divide the batter into 3 8-inch baking pans and bake in a 180c (350f) preheated oven for about 25-30 minutes (depending on your oven) or until a toothpick is inserted into the cake comes out clean.
Let the cakes cool to room temperature and remove them from the pans.
Make the oreo frosting
Into a big mixing bowl, add the room temperature butter, powder sugar, vanilla extract, oreo crumbs, and heavy cream. Mix with an electric hand mixer for a few minutes until the buttercream is light in color and creamy.
Assembly
Pipe a small dollop of the vanilla buttercream on the surface that you will frost on. Lay the first cake layer over the frosting dot.
Top the first cake layer with ⅓ of the buttercream and spread an even layer using a spatula. Repeat with the second cake layer, and top it with the third cake layer.
Frost the cake with a very thin layer of buttercream, and place the cake in the freezer to set for 15 minutes. (this is the crumb coat)
Remove the cake from the freezer and frost it with the remaining frosting and place it in the freezer for another 10 minutes to set.
Pour the chocolate ganache over the cake and use a spatula to carefully push the ganache around the edges of the cake until a drip design forms.
Make dollops of the chocolate whipped cream around the edges of the cake. We used a 1M piping tip.
Top each dollop of whipped cream with an oreo cookie.
Notes
Use room temperature ingredients. It is important that you use room-temperature ingredients like eggs. This step ensures that your mixture mixes into a homogenous mixture and bakes perfectly.
Measure your flour correctly! When measuring your flour, avoid scooping it with a measuring cup. Instead, stir the flour with a spoon to create as many air pockets as possible, and spoon it into your measuring cup. Finally, level it with a back of a knife.
Don’t overmix the batter, you don’t want to develop the gluten in the flour. This step ensures you have a moist cake and not a dense and dry cake.
Line your baking pan with parchment paper! This step helps the cake to bake evenly, and it makes sure that your loaf cake will release easily from the pan.
Make sure that your butter is at room temperature. An hour or two before making these cookies, take the butter out of the fridge and let it come to room temperature. The butter should be soft to the touch. If your butter is too cold, it will be harder to mix and there will be lumps of butter in the dough.
Be patient! I know it’s extremely tempting to frost this cake as it is pulled out of the oven, but let the cake cool for at least 1 hour so it will be more firm and won’t crumble up, and prevent the frosting from melting.