Old Fashioned Cupcakes

I’ve been feeling a little lush lately, and my lust for adventure seems to have focused itself around the cocktail culture of New York City. Despite the lack of income to support such habits, I love the class and the sophistication associated with a proper cocktail party. It’s the history of the Roaring Twenties from whence the contemporary speakeasy was derived, however, that really tickles me. With mobsters, liquor, sex, and scandal, the badass-ery of the era was unsurpassed. Even though it was Prohibition, and liquor couldn’t be spotted in plain sight, people went to great lengths, often erring on the side of illegality, to get their kicks. After all, it was the Golden Age, and what’s more golden than a good jazz sesh and a little libation to loosen things up?

The positive sentiment towards cocktails still reigns supreme in this gritty, glamorous city. We won’t get locked up for throwing back a few every now and then, but we can still enjoy the perks of a good Old Fashioned and an ambient lounge like it’s 1925. One day, When I was serving up an Old Fashioned at my restaurant, I flew into a fit of culinary inspiration, and I came up with the idea for a boozy cupcake. I hadn’t an appropriate event for which to try this idea out until the other week. While my friend was deciding where to celebrate his 33rd birthday, I was deciding how to celebrate it. His being a big fan of bourbon, I knew these ridiculously boozy cupcakes from Serious Eats would be the perfect treat to liven up the birthday festivities.

With the orange-vanilla bourbon-soaked cake, the bitters, and the bourbon buttercream, these cupcakes really nail the flavor of an Old Fashioned. I used a teaspoon of 101 proof Wild Turkey bourbon–that’s right, folks–to soak each cupcake, so as to achieve a proper slosh. Mission accomplished, there. And I upped the zest in the “sawdust” to intensify the orangey freshness. My friends were absolutely thrilled with these drinks–excuse me, cupcakes–and downed the lot of them in about 4.3 minutes. Next time we have an urge to party like the Golden Agers, I have a feeling I’ll be bringing these cupcakes along!

Old Fashioned CupcakesOld Fashioned Cupcakes – makes 12-16
Ingredients for the cake:

  • 1 1/2 cups and 2 Tbs cake flour
  • 1 1/2 tsp baking powder
  • 1/2 tsp salt
  • 12 Tbs (1 1/2 sticks) unsalted butter, softened
  • 1 1/4 cups sugar
  • 3 eggs
  • 1/4 cup and 2 Tbs fresh-squeezed orange juice
  • 1 Tbs orange zest
  • 1/4 tsp orange extract
  • 1 tsp vanilla extract
  • 1/4 cup sour cream (use full-fat)
  • 1/4-1/2 cup whiskey or bourbon (I used Wild Turkey) for soaking the cupcakes

Ingredients for the frosting:

  • 12 Tbs (1 1/2 sticks) unsalted butter, softened
  • 4 1/2 cups confectioners’ sugar, sifted
  • 1/4 cup and 2 Tbs whiskey or bourbon
  • 7-9 dashes of Angostura bitters, to taste 
  • 3/4 tsp orange extract
  • 1/2 tsp orange zest

Ingredients for the “orange sawdust”:

  • 2 Tbs sugar
  • 1 tsp orange zest

To make the cake:
– Preheat oven to 350 and line a muffin tin with cupcake liners.
– In a medium bowl, sift together the cake flour, baking powder and salt, and set aside.
– In a large bowl cream the butter and sugar on medium-high speed until light and fluffy, about 2-3 minutes.
– Add the eggs and beat until well-combined.
– Add the orange juice, orange zest, orange extract, vanilla extract and combine on low speed.
– Add the flour mixture in intervals on low speed, until all the dry ingredients are thoroughly combined.
– Add the sour cream and beat again until combined.
– Fill each muffin cup about 3/4 full.
– Bake for 24 minutes, rotating the pan halfway through.
– Wait until the cupcakes have cooled a bit and poke about 12 holes on the top of each cupcake with a fork.
– Pour 1 tsp of whiskey or bourbon (I used less than the original recipe suggested) on top of each cupcake to soak through.
– Make sure cupcakes are completely cooled before frosting.

To make the frosting:
– In a large bowl or bowl of a stand mixer, cream the butter on medium-high speed until light and fluffy.
– Reduce the speed to low and add half of the confectioners’ sugar, and all of the whiskey, Angostura bitters, orange extract and orange zest, beating until fully combined.
– Add the rest of the confectioners’ sugar and beat on medium-high speed for about 2-3 minutes, or until completely mixed.

To make the “orange sawdust”:
– In a small bowl, thoroughly combine the sugar and orange zest.
– Sprinkle on top of the cupcakes, immediately after frosting.


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