Old Fashioned Cupcakes! Hipster Beard & Round Ice Not Required!

I am back on the sauce…chocolate sauce that is…well chocolate. It’s February, the unofficial or official chocolate month, who knows. There is a day/month for everything. I digress. Back on the sweet eats after taking a month off. I am coming back with a vengeance with these Old Fashioned (as in the cocktail, not like old timey, but I guess old timey cocktail, that is now trendy…) inspired chocolate cupcakes! They are rich, moist, chocolatey, orangey, bourbony, decadence and won’t give you a hangover!

I made these babies for a friend’s bday celebration. She wanted to be a tourist in our own city. Which is great, there are so many things to do and see in Chicago that I haven’t even seen living here. We went on the Chicago Prohibition tour of old speak easy spots around town! Most of the information was known, but what I found very interesting and didn’t know this before, was that on the right side of the law was a woman who was one of the first female Assistant Attorney Generals, Mabel Walker Willebrandt. She was known as one of the highest-ranking women in the U.S. government during the 1920s. She prosecuted the Volstead Act during the Prohibition, sometimes using tax laws to put away top-level rumrunners. Any who, instead of glorifying and romanticizing these murderous criminals of the 20’s and making the same tired old gangster movies, I would be far mor interested in seeing the female perspective on the other side of the law and her experiences during this time! Any who, you can experience these cupcakes without a movie, time machine, prohibition tour or even an old fashioned (although, you will have the ingredients on hand so, do what you will).

Speaking of the ingredients, I use reduced bourbon and bitters in the cupcake batter that adds a depth of flavor and brings out the chocolate flavor beautifully. You won’t get a strong note of bourbon or bitters, but it works well to marry with the other ingredients that enhance the taste. For the frosting, I opted for my all-time fav, light as air, smooth as silk, superhero of a frosting, Swiss Meringue Buttercream. Kept things dark with more cocoa in the frosting, along with a touch more bitters, orange liqueur, because we need more booze in our sweet treats and some fresh orange zest. Man are these darlings delicious!

Orange zest, orange liqueur, chocolate silk oh my!

Skip Bucktown (or your respective hipster hoods) and fighting your way through manicured mustachios and beards this weekend and down that Old Fashioned in cupcake form in the comfort of your own home. Heck go crazy, make that sphere of ice from that mold you just had to have to drop in your left-over bourbon to wash it down with. It is the weekend after all! YOLO (I think that was so 2018, what’s the new obnoxious phrase of 2020 going to be?)

Happy Weekending and Eating Your Old Fashioning It!

Diane

Old Fashioned Cupcakes! Hipster Beard & Round Ice Not Required!

 

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Prep time

25 mins

Cook time

16 mins

Total time

41 mins

 

Author: Diane

Serves: 12

Ingredients

• For the Cupcakes:
• 1⅓ cup AP four
• ½ cup cocoa
• 1 stick butter
• 2 eggs
• 1 cup granulated sugar
• ½ tsp. Salt
• 1 tsp. Espresso powder
• 1 tsp. Baking powder
• ¼ tsp. Baking soda
• 1 tsp. Vanilla extract
• ¼ tsp. Bitters
• ¼ cup buttermilk
• ¼cup whole milk
• ½ cup Bourbon reduced by half
• Chocolate Orange Swiss Meringue Buttercream:
• 4 sticks butter
• ⅓ cup cocoa powder
• 2oz melted bittersweet chocolate
• 1 tbsp. orange liqueur
• 1 tbsp. Orange zest
• 1 tbsp bourbon
• ¼ tsp. bitters
• 1 tsp. Vanilla extract
• ½ tsp. Salt

Instructions

1. For the Cupcakes:
2. In a small saucepan over medium heat reduce the bourbon by half. Remove from heat and allow to cool some.
3. Pre-heat oven to 350 degrees and line a 12 cupcake pan with liners and 4 liners in a second pan, and set aside.
4. In a medium bowl combine the flower, salt, baking powder, baking soda, cocoa powder, espresso and set aside.
5. In a separate bowl, combine, the milk, buttermilk and vanilla extract, bitters, bourbon and set aside.
6. In the bowl of a stand mixer beat the butter until light and fluffy about 3 minutes.
7. Slowly add the sugars and beat to combine, about five minutes. Scrape down side of bowl as needed.Add the brown rice syrup and combine until incorporated. Next add the eggs one at a time and beat until fully combined.
8. Add one third of the dry ingredients and beat until just combined. Next add half of the liquid mixture and beat until combined. Add another third of the dry and beat to incorporate.
9. Next pour in the rest of the liquid and beat until combined. Add the remaining dry ingredients and mix until just combined. Do not over mix.
10. Fill each of liners three fourths full and bake for 16 to 18 minutes until toothpick inserted comes out with an only a few moist crumbs.
11. Allow to cool in pan on wire rack. Remove from pan after 10 minutes to cool completely on rack.
12. For the Buttercream:
13. Separate whites from yolks in the bowl of a stand mixer.
14. Pour sugar in bowl with the egg whites and add the salt.
15. Place bowl over, not touching, a pot with simmering water.
16. Whisk constantly until sugar has completely dissolved around 160 degrees. If you don’t have a candy thermometer, you can tell it’s done when you rub a little of the mixture between your fingers and it is completely smooth with no graininess. Should take about 10 minutes.
17. Then return bowl to stand mixer fitted with a whisk attachment.
18. Begin beating the eggs and sugar until whites are glossy and stiff peaks have formed.
19. The bowl should be cool to the touch, this will take around 10 minutes. While the egg whites are beating, melt the chocolate in a heat proof bowl in the microwave in 30 second intervals until smooth and completely melted. Set aside an allow to cool some.
20. Next switch to the paddle attachment and beat on medium high speed.
21. Add the butter slowly one piece at a time to incorporate. The mixture will look like it’s curdled, keep mixing, that is normal.
22. Mix until frosting is smooth and shiny. Add the cocoa powder and mix to combine. Then add the melted and slightly cooled chocolate.
23. Add in the vanilla extract, bitters, bourbon, orange liqueur and orange zest.
24. Frost the Cupcakes:
25. In a large piping bag fitted with tip of choice, I used a large Star tip, pipe the frosting on the cooled cupcakes and top with more grated orange zest. Serve at room temp. Store cupcakes for 2 days at room temp in airtight container or up to 5 in the fridge.
26. Enjoy!

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