When I say these are old-fashioned cupcakes, I don’t mean old-fashioned like Grandma used to make. Unless Grandma was a whiskey-shooting wild child who liked taking her crazy ideas to the stand mixer so she could have her cake and drink it, too. In which case, yeah, they’re that kind of old fashioned. It’s the kind of grandma I’d want to be.

You can bet your booty there’s bourbon in here— or, in this case, Gentleman Jack whiskey (I’ll explain this choice in a moment). And the frosting? Also boozy, with a generous splash of blood orange bitters and a shot of caramel flavor. Garnished with a candied orange wedge and a cocktail cherry, of course.

I started thinking about these when I baked this year’s batch of mint julep cupcakes for Kentucky Derby, and I will admit that the result of these old fashioned cupcakes exceeds even what my taste buds imagined. They really do taste like the cocktail! The best thing about them is that, despite the complex flavor arrangement, they are surprisingly easy to make. 

What goes into an Old Fashioned cupcake?

For these grownup-only treats, I followed the formula template of my mint julep cupcakes, but with different flavor enhancers. Butter, brown and white sugars, eggs. And then the old fashioned flavors, in the form of orange zest, cocktail cherry syrup and (obviously) the whiskey. Alternate the addition of dry and wet ingredients, a bit at a time, to ensure even mixing; too much of either at once and you’ll end up overmixing the batter.

As an aside, do you see what my KitchenAid did with the zest? I guess it’s best to stir that in by hand at the end! Divide the batter evenly among the cupcake liners and bake, then cool for a bit before transferring them to a wire rack.

Why whiskey rather than bourbon?

We’ve enjoyed many a cocktail with Gentleman Jack, and I got curious what kept it from being labeled as bourbon. It is, after all, 80% corn and aged in oak barrels, and obviously produced in the U.S., so it certainly qualifies to be called “bourbon,” but the folks at Jack Daniel’s like to point out that their whiskey is charcoal-mellowed, and they consider it to be superior in every way to bourbon.

I don’t necessarily agree, but Gentleman Jack is very easy on the palate, and lower proof (80) than most of the bourbons we usually drink, which makes it lovely with the sweetness of dessert. Boozy, but no harsh bite. Now, let’s talk about the caramel notes in this buttercream!

The icing on the (cup)cake

Buttercream is not as difficult as I once feared—at least, not the kind I make. The butter should be softened at room temperature for about half an hour, so that you can press a fork or finger into it and leave an indent without the butter losing its shape. I use salted butter to accent all the other flavors.

For an “old fashioned” vibe, I spiked the butter with dulce de leche to accentuate the warm caramel flavors of the whiskey. Whip those together with an electric mixer until it is soft and fluffy before adding the sugar. If you go too far with powdered sugar, you can smooth it out again with a few drops of cold heavy cream. You want it swirly, but stable.

The finishing touch for my old fashioned cupcakes was a drizzle of Gentleman Jack and a spoonful of Stirring’s blood orange bitters. These are sold in a larger bottle than typical bitters, and they’re non-alcoholic, which makes them less intense. This is what really gives a “cocktail” flavor to the cupcakes, perhaps even more so than the star ingredient of whiskey. If you can only get regular, alcohol-based bitters, use half as much.

Decorating the cooled cupcakes is easy as well, and if you don’t have a piping bag with a star tip, don’t sweat it. Load up a zip-top bag and snip the corner. Or go old school and swirl a massive amount on with the back of a spoon. Just keep a stack of extra spoons on standby because, no matter how restrained you think you are, you’ll be licking them. Add the candied oranges and cherries when you’re ready to serve. Cheers!

Old Fashioned Cupcakes

• Servings: One dozen
• Prep Time: 45 minutes total
• Cook Time: 20 minutes
• Difficulty: Average
• Print

Whiskey, orange zest and cocktail cherries give these easy cupcakes a distinctive, 'old fashioned' flair, complete with orange bitters-accented buttercream and a cherry on top!

Ingredients

• 1 1/2 cups all-purpose flour
• 2 tsp. baking powder
• 2 pinches kosher salt
• 1/2 cup (1 stick) unsalted butter, softened
• 1/2 cup sugar
• 1/2 cup brown sugar
• 2 eggs, room temperature
• 1/4 cup Gentleman Jack Tennessee whiskey (or lower proof smooth bourbon)
• 1 tsp. real vanilla extract
• 1 Tbsp. Luxardo cocktail cherry syrup (see notes)
• 1/4 cup whole milk, room temperature
• 1 Tbsp. finely grated orange zest
• 1 recipe orange bitters buttercream (below)
• 4 candied orange slices, quartered (I found these at Trader Joe’s)
• 12 cocktail cherries, blotted on paper towel

Notes: The cocktail cherry syrup I used is very thick, like pancake syrup. If using thin syrup, reduce amount of whiskey or milk.

Directions

1. Preheat oven to 350° F, with oven rack in center position. Line 12-muffin tin with double cupcake papers.
2. Combine flour, baking powder and salt in a medium bowl and whisk to combine. Set aside.
3. In a stand mixer, or a bowl with hand mixer, cream butter until softened. Add brown and white sugars gradually, beating continually. Stop to scrape down bowl twice. Add eggs, beating after each. Stream in whiskey and cocktail cherry syrup. Scrape down bowl.
4. Add 1/3 of the flour mixture and beat on low just until incorporated. Beat in half of the milk, then repeat with half of remaining flour, more milk, last of flour. Stop mixer and scrape down bowl, folding in the orange zest at the end.
5. Divide batter into lined muffin cups. They will be roughly 3/4 full. Bake 18 to 22 minutes; cupcakes are finished when they pass the toothpick test.
6. Cool in pan for about 15 minutes before transferring to a wire rack to cool completely.

Ingredients

• 1/2 cup (1 stick) salted butter, softened at room temperature
• 2 Tbsp. dulce de leche
• About 4 cups confectioner’s sugar (depending on desired consistency)
• 3 tbsp. Gentleman Jack
• 2 tsp. Stirrings blood orange bitters (or 1 tsp. regular orange bitters)
• Heavy cream, if needed to thin icing to desired consistency

Look for dulce de leche in the canned milk aisle, or use a sticky caramel topping as a substitute. You could also omit this if you don’t mind giving up the caramel accent.

Directions

1. Using the whip attachment of a stand mixer, or whip beaters of a handheld mixer, cream the butter and dulce de leche until soft and fluffy.
2. Add half of the confectioner’s sugar and beat until incorporated, then stream in whiskey and orange bitters. Add remaining sugar a few spoonfuls at a time until you achieve desired consistency. If you overdo it, whip in a tablespoon or more heavy cream.
3. Pipe or spoon buttercream onto cupcakes, and garnish them with the candied orange slices and cocktail cherries.