The “Don Draper”

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{Whiskey-Soaked Cupcakes with Old-Fashioned Buttercream and Orange Sawdust }

My friends and I are big fans of Mad Men. When the final season (part 1) started, I made these cupcakes for our Mad Men party. I will warn you right now: these are the most alcoholic cupcakes I have ever made. I dabble in a lot of boozy baked goods, but I could actually feel the heat of this one when I took a bite. The cake itself is soaked with whiskey, in addition to the alcohol in the buttercream. Still, I don’t think it was a turn-off, because the orange spongey cake and the orange sawdust topping gave it that sugary kick.

I searched the web for the best Old Fashioned cupcake recipe, and came across this one from Serious Eats. For the reasons stated above, I could tell it was going to be the most authentic way of replicating the cocktail in baked-good form.

Yields 24 cupcakes.

For the cupcakes:

  • 1 1/2 cups plus 2 tablespoons cake flour
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 12 tablespoons (1 1/2 sticks) unsalted butter, softened
  • 1 1/4 cups sugar
  • 3 large eggs, broken into a small bowl
  • 1/4 cup plus 2 tablespoons freshly squeezed orange juice, from 3 large oranges
  • 1 tablespoon orange zest, from 1 large orange
  • 1/4 teaspoon orange extract
  • 1 teaspoon pure vanilla extract
  • 1/4 cup full-fat sour cream
  • 1/4 to 1/2 cup whiskey, such as Jack Daniel’s

For the icing:

  • 12 tablespoons (1 1/2 sticks) unsalted butter, softened
  • 4 1/2 cups confectioners’ sugar, sifted through a strainer
  • 1/4 cup plus 2 tablespoons whiskey, such as Jack Daniel’s
  • 9 dashes Angostura bitters
  • 3/4 teaspoon orange extract
  • 1/2 teaspoon orange zest
  • 2 tablespoons sugar
  • 1/2 teaspoon grated orange zest

 

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Cupcake directions:

  1. Preheat the oven to 350°F. Line muffin pan with cupcake liners.
  2. In a medium mixing bowl, sift together the cake flour, baking powder, and salt. Set aside.
  3. In another medium-size mixing bowl, with an electric mixer on medium-high speed, beat the butter and sugar together until light and fluffy, 2 to 3 minutes.
  4. Scrape down the sides of the bowl, and add the eggs, beating until combined.
  5. Add the flour mixture, orange juice, orange zest, orange extract, and vanilla, beating on low speed just until all the dry ingredients are incorporated.
  6. Add the sour cream and beat again to incorporate, scraping down the sides of the bowl as needed.
  7. Fill each prepared muffin cup with a rounded 1/3 cup batter, about 3/4 full.
  8. Bake, rotating the pans halfway through, until the tops are just firm to the touch and a tester inserted in the center of a cupcake comes out clean, about 24 minutes.
  9. Allow cupcakes to cool completely.
  10. Using a toothpick, poke about 15 holes in the top of each cupcake and slowly spoon 1 to 2 teaspoons of the whiskey over the top of each cupcake. Let them sit for 10 minutes to allow the whiskey to be absorbed.

Out of the oven:

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After poking the holes:

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Icing directions:

  1. In a large-size mixing bowl, with an electric mixer on medium-high speed, beat the butter until light and fluffy.
  2. Scrape down the sides of the bowl, reduce the speed to medium, and add half of the confectioners’ sugar, the whiskey, bitters, orange extract, and orange zest, beating to incorporate.
  3. Add the rest of the confectioners’ sugar, beating on medium-high for 2 to 3 minutes until very smooth and creamy, scraping down the sides of the bowl as needed.
  4. To make the orange sawdust, mix together the sugar and the orange zest (see yellow bowl picture).
  5. Frost cupcakes, and use a spoon to sprinkle the orange sawdust on top.

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