Little Bayley called me up this week and asked if I would make cupcakes for her boyfriend’s birthday… silly question of course.  I thought about their relationship for a bit and one thing stuck out: their mutual love of whiskey. As a fan of alcoholic baked goods in general, I figured this could be a very fun adventure.

A few searches led me to this recipe, which sounded absolutely amazing – I mean, coffee AND whiskey? Yum! Clearly I had to modify it to make it my own though, so as I was whisking the chocolate mixture I was inspired to add a bit of cinnamon and cayenne pepper (similar to Mexican Hot Chocolate). Now that’s a wicked cupcake.

Wicked Whiskey Cupcakes Final

These turned out heavenly – just a hint of the spices in the moist cake, plus a nice Jack Daniel’s flavor in both the frosting and the cupcake to bring the whole thing together. They aren’t too spicy nor are they overwhelmingly chocolatey, but you could adjust amounts based on your preferences.

Chocolate Wicked Whiskey Cupcakes
(Adapted from Piratecupcake on Bakespace.com)

Cooking Time: 30 Minutes
Servings: About 32 Regular Cupcakes

The most important ingredients

  • 1 cup unsweetened cocoa powder (get the good stuff, it’s worth it)
  • 1 cup brewed coffee
  • 1 cup of American whiskey (I used Jack Daniel’s, but you can pick your own poison)
  • 2 Sticks of unsalted butter cut in to one inch pieces.
  • 2 Cups of sugar
  • 2 Cups of all-purpose flour
  • 1 1/4 teaspoons baking soda
  • 1/2 teaspoons salt
  • 2 Large eggs
  • 1 teaspoon vanilla
  • 1/2 teaspoon of cinnamon
  • 1/4 teaspoon of cayenne pepper (to taste)

Put oven rack(s) in middle position and preheat oven to 325F.

Melt the butter

Heat coffee, whiskey, butter, and cup of cocoa powder in a 3-quart heavy saucepan over moderate heat, whisking until butter is melted. Remove from heat, then add sugar and whisk until dissolved, about 1 minute. Transfer mixture to a large bowl and cool 5 minutes.

All 3 components ready to be whiskedy

While chocolate mixture cools, whisk together flour, baking soda, and salt in a bowl. Whisk together eggs and vanilla in a small bowl, then whisk into cooled chocolate mixture until combined well. Add cinnamon and cayenne pepper. Add flour mixture in thirds, whisking after each addition, and whisk until just combined (the batter will be a bit thin and bubbly).

Thin and bubbly batter

Scoop cupcakes into lined cupcake pans, filling from 1/2 to 2/3 full. I like to use my ice cream scoop for this, just be careful of drips with this batter.

Two pans and an ice cream scoop

Side Note: As you can see, I have two cupcake pans, but one is darker than the other. I know that this darker one tends to cook faster, so I filled the light one first, put it in the oven with a 30 minute timer, then filled the dark one and put it on the rack above. That way both batches were ready at the same time!

Bake Cupcakes for 30 to 40 minutes. They are ready to go when a toothpick inserted in the center comes out clean. Place them on a rack to cool and then ice with my JD Fudge Frosting or just dust with powdered sugar.

JD Fudge Frosting

I’ll be honest, this frosting stemmed from a pure desire to use up my leftovers. I had extra fudge leftover from making Peanut Butter and Fudge Oatmeal Cookies, and I was certain I could make it into a great frosting. This recipe will act like you are starting from scratch in case you’re not a hoarder like me.

  • 1 cup chocolate chips
  • 1/2 14oz can of fat free sweetened condensed milk
  • 2-3 tablespoons of Jack Daniel’s (or any other whiskey)
  • 3 cups of powdered sugar

In a small saucepan over low heat, combine the chocolate chips and the condensed milk. Stir regularly until you have a creamy, homogeneous fudge mixture. Remove from heat and transfer the fudge to a medium bowl.

Jack Daniel's Fudge Frosting

Add the half of the Jack Daniel’s and half of the powdered sugar and mix with an electric mixer. Add more whiskey to taste and more powdered sugar until you reach your desired consistency. I found that this frosting did not pipe well, but did smooth out into a beautiful frosting shell.

Finished, decorated cupcakes!

Decorate the cupcakes as desired – I used red sugar to keep the wicked, spicy theme going. Enjoy!

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