Decadent and moist, baked with bourbon, orange extract, espresso, and cocoa and finished with a sweet honey-orange buttercream frosting- this cake replicates the bold flavors of an Old Fashioned cocktail. —Alyssa
Preheat oven to 325 degrees. Grease two round cake pans with unsalted butter and coat with a dusting of unsweetened cocoa powder. Roughly chop all the chocolate and in a double boiler over 1 cup of simmering water, melt chocolate. Save water and set chocolate aside to cool. In a bowl, whisk together espresso and cocoa powders. Reboil simmer water if cool and pour water into the espresso and cocoa mixture. Stir until dissolved. Add whiskey and salt to the mixture and let cool.
Using an electric mixer, beat softened butter until fluffy. Add sugar and mix on medium speed until well combined. In a separate bowl, whisk eggs. Slowly pour eggs into the sugar mixture until combined. Beat in the vanilla extract, orange extract (if using), baking soda and melted chocolate. On low speed, slowly alternate beating in some flour and some bourbon mixture until all is combined and has a mousse-like consistency. Pour into prepared pans and smooth top. Bake for about 50-55 minutes or until a cake tester inserted into center of cake comes out clean.
Transfer cake to a rack and let cool completely. For the buttercream, beat softened butter in a mixer until fluffy. Add in remaining ingredients and beat until smooth and fluffy. Frost one of the cake layers and stack the other on top. Refrigerate for 30 minutes before frosting the outside to avoid cake crumbles. Decorate with orange twists.