Preheat the oven to 350°F (175°C) and prepare the pan(s) you plan to use (9-inch or 8-inch round, or muffin pan) by greasing and/or lining them.
In a very large bowl, combine the devil's food cake mix, 3.9-oz package of Jell-O instant chocolate pudding mix, sour cream, vegetable oil, eggs, 1/2 cup milk, and 1 tsp vanilla. Mix until a thick, uniform batter forms.
Pour the batter into your prepared cake pan(s) or into the muffin pan, filling as appropriate for the pan size.
Bake using the time guideline on the back of the cake mix box for your chosen pan; begin checking doneness with a toothpick at the suggested time and then every 5 minutes until a toothpick inserted in the center comes out clean or with a few moist crumbs.
Remove the cake(s) from the oven and allow to cool completely on a wire rack before frosting.
To make the buttercream frosting, place 1 cup room-temperature butter in the bowl of a stand mixer fitted with the paddle attachment and beat on medium speed until smooth and creamy, about 2 to 3 minutes.
With the mixer on low, add 6 cups powdered sugar, 1/2 cup whipping cream, and 2 tsp pure vanilla extract. Mix until the frosting is light and fluffy.
If the frosting is too thin, gradually add additional powdered sugar until you reach the desired consistency; if too thick, add a little more cream, 1 tsp at a time.
Frost the cooled cake or cupcakes as desired.