Grease three 8-inch round cake pans and line bottoms with parchment paper.
In a large mixing bowl, combine the sugar, flour, cocoa, baking powder, and baking soda. Add the eggs, cream, and oil; beat on medium speed for 2 minutes. Stir in the whiskey and black coffee. The batter will be thin.
Pour the batter into the prepared pans.
Bake 30 - 35 minutes, or until a wooden pick inserted in the center comes out clean. Cool on a wire rack for 10 minutes before removing from pan.
Salted Caramel Whiskey Syrup:
Combine whiskey, sugar, and butter in a small saucepan and bring to a boil. Remove mixture immediately and let cool.
In a saucepan over low heat, melt butter. Add brown sugar and continue to cook on low heat stirring constantly for 2 minutes, or until sugar is dissolved. Remove from heat and let cool. Stir in the powdered sugar and whiskey. Add the milk a tablespoon at a time until you reach a desired frosting consistency.
Brush the syrup over the top of each layer letting it soak in a bit. Spread a layer of the caramel over two of the layers and stack the layers on top of on another, the unfrosted layer of top.
Frost the cake with your favorite chocolate frosting. Drizzle some caramel syrup down the sides of the cake and garnish with caramel corn for a touch of whimsey.