First tasted these years ago and then my friend, Lindsey, was kind enough to provide the recipe. I messed with it a bit, admittedly. And these are probably the most complicated cupcakes I’ve ever baked but they’re simply made in 3 stages and not actually difficult at all. Trust me, the effort is worth it.

(original recipe from SmittenKitchen.com)

Ingredients:

Guinness Chocolate Cupcakes
1 cup stout (such as Guinness)
1 cup (2 sticks) unsalted butter
3/4 cup unsweetened cocoa powder
2 cups all purpose flour
2 cups sugar
1 1/2 teaspoons baking soda
3/4 teaspoon salt
2 large eggs
2/3 cup sour cream

Irish Whiskey Ganache Filling
16 ounces bittersweet chocolate
1 1/3 cup heavy cream
4 tablespoons butter, room temperature
2 to 4 teaspoons Irish whiskey (optional)

Baileys Frosting
3 to 4 cups confections sugar
1 stick (1/2 cup or 4 ounces) unsalted butter, at room temperatue
3 to 4 tablespoons Bailey’s Irish Cream (substitute milk or heavy cream for non-drinkers)

Special equipment: 1-inch round cookie cutter or apple corer

Cupcake Directions:
(can be made up to 1 week in advance and frozen until ready to serve).

Preheat oven to 350°F. Line 24 cupcake cups with liners.

In a heavy, large saucepan, bring 1 cup Guiness stout and 1 cup butter to simmer over medium heat. Whisk in cocoa powder until mixture is smooth. Remove from heat and allow cool slightly, whisking every couple of minutes during the cooling process.

In a large bowl, combine flour, sugar, baking soda, and 3/4 teaspoon salt. Use a clean whisk to thoroughly mix these and prevent streaks in the batter from the baking soda.

In another large bowl, beat eggs and sour cream until well-blended. Add cooled stout-chocolate mixture to egg mixture and beat just to combine.

Add flour mixture a little at a time while beating briefly on slow speed.

Divide batter among cupcake liners, filling them 2/3 to 3/4 of the way.

Bake at 350 until tester inserted into center comes out clean, rotating them once front to back if your oven bakes unevenly, about 17 minutes. Cool cupcakes completely on a rack.

Filling Directions:

Coarse chop the chocolate and transfer it to a heatproof bowl. In a small saucepan, heat heavy cream until just simmering and immediately pour over chocolate. Let sit for one minute, then stir until smooth. (Note: If this has not sufficiently melted the chocolate, heat mixture in a double-boiler to gently melt what remains. 20 seconds in the microwave, watching carefully, will also work.) Add the butter and whiskey (optional) and stir until combined.

Fill the cupcakes…

Let the ganache cool until thick but still soft enough to be piped (refrigeration will speed this along but you must stir it every 10 minutes).

Meanwhile, using 1-inch round cookie cutter or an apple corer, cut the centers out of the cooled cupcakes. Note: You want to go most of the way down the cupcake but not cut through the bottom — aim for 2/3 of the way. A slim spoon or grapefruit knife will help you get the center out. Set them aside to re-top the cupcakes after filling.

Put the ganache into a piping bag with a wide tip and fill the holes in each cupcake, dividing the ganache evenly between 24 cupcakes. (A large freezer bag with a tiny bit of the corner cut off can also substitute for a piping bag)
Once filled, replace the tops to each cupcake. (Possibly remove some of the inner cake to allow the top to sit even on the top of the cupcake.)

Frosting Directions:

Whip the butter in the bowl of an electric mixer, or with a hand mixer, for several minutes until very light and fluffy. Slowly add the powdered sugar, a few tablespoons at a time.

When the frosting looks thick enough to spread, drizzle in the Baileys (or milk) and whip until combined. If this has made the frosting too thin beat in another spoonful or two of powdered sugar.
Ice and decorate the cupcakes.