Chocolate Whiskey Cupcakes

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 🙂

Chocolate Whiskey Cupcakes
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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

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.

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

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.

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.

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.

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.

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.

Source: cupcakes adapted from Baking Illustrated, frosting adapted from The Pastry Queen by Rebecca Rather

56 Responses

  1. Your co-workers are really lucky to have someone like you brighten their birthdays!! (green with envy…ha ha)

  2. I am in awe of your ability to cook such fabulous food, and hold down a job and raise a baby! Amazing. As for these… I’m intrigued. I really enjoy chocolate and Kahlua, so I wonder about the whiskey too… interesting!

  3. Gotta love the boozy cupcakes with chocolate! They look so yummy!

  4. I’ve made frosting like this in the past when I worked as a professional pastry cook. We used small saucepans with a pour spout (like you would use for melted butter) for the sugar mixture. As long as you are careful and your saucepan is clean to start, you can pour directly from the saucepan into the mixer with no problem. We used to aim for the ‘sweet spot’ in the mixer – the area between the bowl and where the paddle/beater are rotating so all of the mixture went into the eggs and not stuck on the metal parts.

  5. These look super yummy…I’m not sure if I could handle the whisky though!!!

  6. OMG, these look amazing. I have to ask, what size tip do you use to frost your cupcakes? I can never get mine to look that nice! Also, are these regular size, or mini cupcakes? Either way, I’m sure they were delicious, and your coworkers are a lucky bunch!

    • Hi Emily,
      I don’t know what number this tip was. I’m pretty sure it doesn’t have a size on it. These are full size cupcakes, but of course you can make them mini.

  7. Hi Annie. I discovered your blog several weeks ago and love the fact that you post so often. So many great ideas! I have a quick question on this one – what decorating tip did you use? Any advice on technique? I’ve piped icing before but never just one big star. It definitely takes the look up a step. Thanks!

  8. These are gorgeous!! I love how you’ve piped on the frosting! Do you remember what kind of/general size tip you used? I’m trying to think if I have one that would make that pattern… The whiskey simple syrup is a great idea, especially for cupcakes to keep them super moist.

  9. MMm I have had my eye on that buttercream since I got her cookbook too. Jack Daniels is my husband’s fave. I never would have thought to pair it with chocolate though – genius! Will you let me know how it works if you just add it to the icing? I have done it in the past with tequila and bourbon, and it seems to thin out the icing too much to pipe on very well. The only alcohols that haven’t done that have been the cream based ones.

  10. These look great! It’s funny – I was wondering what size tip you used for the frosting too! I’ve never been able to frost cupcakes as well as you do, I guess that’s a reason to make more cupcakes!

  11. Hey Annie,
    I love, love, love your blog! The very first thing I do in the mornings when I get to work is read your blog. I made the Irish Car Bomb Cupcakes for St. Patrick’s Day for my co-workers. I received emails all day long about how wonderful they were. The cake was so incredibly moist. It was awesome, so I was very excited when I came to work this morning, got online, and saw these yummy looking cupcakes!! Thanks!

  12. Annie, these look picture perfect! I like your method of adding the booze via simple syrup. I’ll have to give that a try, so much easier than guessing how much to add to batter and having the flavor evaporate while cooking. As for the many curious people wondering about your piping tips (including me!) perhaps you could oblige us with a simple photo of the tips you use each time you frost cakes, or a photo of you frosting them so that we could see your technique. Thanks a lot for sharing these yummy bites.

  13. Annie-
    Since I live in Louisville, I plan to try this with my favorite Kentucky Bourbon…Knob Creek !

    I believe the answer to everyone’s question about what tip you use is a Wilton 1M tip. That’ll settle it! :p

    Hope you have a great weekend!!

  14. These look wonderful! Just out of curiosity, these (and the car bomb cupcakes) seem like the recipe from Smitten Kitchen… what is the etiquette on using and/or modifying recipes from other blogs?

    • Emily,
      If you see at the bottom of each recipe, I have listed a source. If I change things about the recipe (either ingredients or my instructions/methods), it says “adapted from”. Yes, the car bomb cupcakes are from Smitten Kitchen and they are linked at the bottom of that post. The food blogging world is one big world of sharing recipes.

  15. Whiskey cupcakes.. I’m intrigued! These look beautiful!

  16. oh yum! I love the look and sound of these cupcakes!

  17. I made the Irish car bomb cupcakes a few weeks ago and they were amazing. This whiskey buttercream sounds awesome too! I’ll have to try this. 🙂

  18. I LOVE your cupcakes!

    I thought I would let you know…I made the Car Bomb cupcakes for my husband’s birthday last fall and inadvertently left out the cocoa. (Oops!) I made a second, chocolaty, batch, and we actually liked them better without. Being chocolate lovers, we were quite surprised!

  19. I will try that recipe for sure.Great presentation!I love your blog!

  20. My Dad would absolutely love these! Chocolate and whiskey are two of his favourite things. I love your piping with the frosting as well. Beautiful!

  21. Lucky co-workers, and how nice of you to do this for everyone! I love that everyone can pick their own type!

  22. So funny – I was just so upset with myself for missing the boat on making a similar cupcake for St. Patty’s Day…but as the baker in the office as well – a co-worker’s birthday is brilliant! I think it’s safe to say any male would appreciate those! xxSAS

  23. Ooh the cupcakes are so pretty! I wish I could have one right now!! 🙂

  24. This sounds fantastic and looks adorable. I wish I had one (who am I kidding? more like 3) in front of me now 8).

  25. uh oh….this will cause a DWC (driving while cupcaked!) 🙂

  26. These are beautiful. Sometimes I make whiskied chocolate milk, so I know all the flavors work too!

  27. so beautiful and simple! What size tip did you use to pipe your buttercream? absolutely lovely.

  28. Hey Annie…I was just wondering if the frosting will hold its shape if I were to omit the two large yolks and just use 2 large eggs? Thanks!

    • Rowina,
      I think that would have a pretty significant effect on the frosting. I’d probably just try a different recipe if you have a problem using the egg yolks.

  29. these look incredible! and such a lovely blog!

  30. These look delicious! I made Chambord icing a few weeks ago that was wonderful. Liquors work so well for frosting flavors. 🙂


  31. I love the look of your icing. What size of tip did you use? I have been looking to for a larger tip for some time now.

  32. How unique! They look amazing!

  33. Gorgeous, delicious-sounding cupcakes!

    I know you said that it wasn’t Wilton, and I have a 1M tip, which wouldn’t be big enough to frost cupcakes the way you did, but what kind/brand of frosting accoutrements do you use?

    • Avi,
      I have frosting tips from several different brands, stores, etc. Most are Wilton but this one isn’t. I don’t remember where I got it.

  34. Wow…those look so cute! I am curious about the chocolate whisky combo…Must try!

  35. I made a half-batch of these cupcakes last night (using the Bailey’s Buttercream icing recipe, substituting whiskey for Bailey’s), and they are amazing! Thanks for another great recipe, Annie!

    • Great! I’m happy to know the whiskey worked well in place of the Bailey’s. I’ll have to try that next time!

  36. And I thought I was so clever… I made a similar recipe last week!

  37. Most Darling Annie-
    I read you everyday and religiously make your sugar cookies (they ARE the best) and royal icing along with your chewy chocolate chip cookies and a few of your other treats. I also love to decorate cakes and cookies, but am new to it. I have a request…would it be possible to let us know which pastry tips you use? These cupcakes are great and I love the frosting…looks almost like a meringue topper, but am curious as to the size tip.

    • Hi Kristen,
      Thanks for the sweet comment. If you read the comments above, you’ll see that a LOT of people have asked what tip I used. Unfortunately, I don’t remember where this one came from and it is not labeled with a number or brand. In general I use a large star tip for all my cupcakes, and this is just a variation on that.
      🙂 Annie

  38. I made these cupcakes for a potluck tonight (and took the suggestion of adapting the Bailey’s frosting). They turned out perfectly! Just the right whiskey flavor. And the chocolate cupcakes were great–moist but not heavy. Definitely recommended!

  39. These cupcakes look great! Does the whiskey taste come through, though?

  40. Annie, this may be a weird question but, do you think that this cupcake recipe could be semi-easily transformed into a cookie recipe? I love to bake and these totally remind me of something my boyfriend would love – except he doesn’t like cupcakes (ugh!). I always want to try some fun recipes like this but don’t want them to go to waste – and I sure can’t eat 24 cupcakes on my own!

  41. Annie, I have been lurking on your blog for months and finally have gotten my act together to move from computer to kitchen! As a fairly experienced cook/baker, I was surprised that these cupcakes gave me some trouble. They taste amazing, but they are all sunken in the middle. I’m sure they are baked through, and most of the sins are covered by the frosting. I was just curious if that was expected with this batter, or if I need to keep trying to perfect my execution. Thank you for your wonderful blog!! As a mother of two who works full-time outside my home, I don’t know how you do it! (But I love that you do!)

    • Kristin,
      I have had other friends and readers mention the sinking issue to me as well. I recently made them again myself to test this, and though they didn’t sink at all for me, they were flat and not domed like many cupcakes. So yes, I guess expected in this case and best covered by frosting, but if you want a better shaped chocolate cupcake I would use the base of the triple chocolate cupcakes instead.

      • Thanks so much. The flavor and texture are so perfect, I can’t see myself settling for another. I will frost right over the little sink hole, and nobody will ever know the difference! (As a side note, there will be orange and yellow butterflies topping these — also from your site — so it should be no trouble hiding the dents!) Thanks again!

  42. Annie,
    I made these cupcakes over the weekend (without the whisky), and they fell on me! The only thing I was missing was just slightly less the 1/4 cup of sugar (I ran out!) but I figured that was ok since the icing I was using was super sweet. But they were all inverted!
    Any ideas why?

    Thank you!

  43. Thanks Annie! Glad to see it wasn’t only me!
    My husband said it’s because we were walking around in the kitchen! He thinks all baking is like a souffle! 🙂

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