I’ve been having a lot of fun playing cupcake fairy for my coworkers on their birthdays.  It’s always interesting to see what flavors people will choose, and I especially love it when I’m challenged to create a new variety I haven’t tried before.  My good friend and coworker Adam has been looking forward to his birthday cupcakes for months.  He also changed his mind several times about what he wanted.  Initially he was leaning toward something uber chocolatey, but after trying the Irish car bomb cupcakes he was loving the idea of a boozey cupcake too.  When I saw a recipe for Jack Daniels buttercream, I knew I had found just the thing.  I ended up making a chocolate cake, brushing it with a whiskey simple syrup, and topping with this fabulous buttercream.  The end result was just what I was hoping for – a moist chocolate cupcake with a nice kick of whiskey.

Everyone seemed to really enjoy these, although it is obvious that people have very different thresholds for the strength of whiskey.  Some thought they tasted very strong, while others (Adam) felt they could have been even stronger.  However, I doubled the amount of whiskey in the frosting and am sure that if I had added even one teaspoon more, it would have dissolved.  Personally, I thought the balance was just right for my tastebuds – strong enough that it deserved the word “whiskey” in the title, but not so strong I was looking for a chaser.  I will say that the frosting was a bit challenging to make.  Though I boiled my sugar mixture to the correct temperature by my candy thermometer, it almost completely hardened when I transferred it to the liquid measuring cup.  I thought all was lost, but decided to try to salvage it anyway.  I added the mixture to the frosting anyway, and it seemed to correct itself because the frosting was perfectly smooth and there were no hard bits of sugar anywhere.  Next time I may just avoid the hassle altogether and use the same recipe as the Bailey’s buttercream, just subbing whiskey instead.  Or maybe mix some Jack into my favorite basic Swiss meringue buttercream.  I think there are lots of options to make these, and they’ll all be delicious because apparently whiskey and chocolate is a winning combination :)

  • Yield 24 cupcakes


For the cupcakes:

  • 1 cup unsweetened cocoa powder
  • 2 tsp. espresso powder
  • 1 cup boiling water
  • ½ cup sour cream
  • 2 tsp. vanilla extract
  • 1¼ cups all-purpose flour
  • ¾ tsp. baking soda
  • ½ tsp. salt
  • 16 tbsp. unsalted butter, at room temperature
  • 1¾ cups sugar
  • 2 large eggs

For the whiskey simple syrup:

  • ½ cup water
  • ½ cup sugar
  • 2 tbsp. whiskey

For the frosting:

  • 2 large eggs, at room temperature
  • 2 large egg yolks, at room temperature
  • ¼ cup water
  • 1 cup sugar
  • 3 sticks (18 tbsp.) unsalted butter, at room temperature
  • Pinch of salt
  • 3-4 tbsp. whiskey


  • 01

    To make the cupcakes, preheat the oven to 350˚ F.  Line two cupcake pans with paper liners (24 total).  Combine the cocoa powder and espresso powder in a small bowl.  Add the boiling water and whisk until the mixture is smooth.  Set aside and let cool to room temperature.  Once cool, whisk in the sour cream and vanilla extract.

  • 02

    Combine the flour, baking soda and salt in a small bowl.  Stir together with a fork to combine; set aside.

  • 03

    In the bowl of a stand mixer fitted with the paddle attachment, combine the butter and sugar.  Beat on medium-high speed until light and fluffy, 3-5 minutes.  Beat in the eggs 1 at a time, beating well after each addition and scraping down the bowl as needed.

  • 04

    With the mixer on low speed, mix in the dry ingredients in three additions, alternately with the cocoa-sour cream mixture, beginning and ending with the dry ingredients.  Beat each addition just until incorporated.  Divide the batter evenly between the prepared cupcake liners.  Bake 18-20 minutes, until a toothpick inserted in the center comes out clean.  Let cool in the pan 5-10 minutes, then transfer to a wire rack to cool completely.

  • 05

    To make the simple syrup, combine the water and sugar in a small saucepan.  Heat over medium-high heat, stirring occasionally, until the mixture is warm and the sugar has dissolved.  Remove from the heat and stir in the whiskey.  Set aside and let cool until ready to use.

  • 06

    To make the frosting, combine the eggs and egg yolks in the bowl of a stand mixer fitted with the whisk attachment.  Whisk on high speed about 5 minutes.  In a small saucepan, combine the water and sugar.  Heat, stirring frequently, until it reaches the soft-ball stage, 234˚-239˚ F.  Immediately transfer the sugar syrup to a liquid measuring cup.  With the mixture on low speed, add the sugar mixture to the egg mixture in a slow, thin stream.  Increase the speed to medium and beat about 7 minutes, until the syrup has cooled and the bowl is just barely warm to the touch.  Add the butter 3-4 tablespoons at a time, beating well after each addition, at least 30 seconds.  Once all of the butter has been added, continue to beat on medium speed until the frosting thickens slightly, 3-5 minutes.  Blend in the salt and whiskey.

  • 07

    To assemble the cupcakes, brush the cooled cupcakes with the whiskey syrup.  Pipe the frosting onto the cupcakes using a pastry bag.  Refrigerate until ready to serve.