Bourbon-O's (Chocolate Sandwich Cookies with Bourbon Cream)

October  3, 2014
5 Ratings
  • Makes 2 dozen sandwich cookies
Author Notes

Tucked away in the corner of my grandmother's kitchen, there was an old, heavy ceramic cookie jar. It had a cracked lid that had been glued together too many times to count, thanks to all the tiny hands (mine included) that had attempted to lift it only to have it slip and fall on the floor. That crashing sound would rudely announce to the aunts and mothers, who were distracted with various cooking tasks, that a pre-dinner cookie heist was underway.

But when my grip on the lid was strong enough, the reward was an overwhelming bounty of Oreo cookies. Here, I've updated the classic sandwich cookie with a hearty swig of bourbon for a boozy touch–but just to keep everyone happy, this recipe is designed so that half the filling stays booze-free. I usually stay clear of vegetable shortening in my baking, but in this recipe it really is essential to make the filling creamy and smooth. If you are truly averse, however, butter is a fine substitute. —buttermeupbk

What You'll Need
  • For the cookies:
  • 1 1/4 cups flour
  • 1/2 cup unsweetened cocoa powder
  • 3/4 teaspoon baking soda
  • 1/4 teaspoon baking powder
  • 1/4 teaspoon espresso powder
  • 1/4 teaspoon salt
  • 8 tablespoons unsalted butter, softened
  • 3/4 cup sugar
  • 1 egg
  • 1/4 teaspoon vanilla extract
  • For the filling:
  • 4 tablespoons unsalted butter, softened
  • 1/4 cup vegetable shortening
  • 2 cups plus 1/3 cup powdered sugar
  • 1 vanilla bean, seeds scraped
  • 1 teaspoon vanilla extract
  • 2 teaspoons bourbon
  1. Sift together flour, cocoa powder, baking soda, baking powder, espresso powder, and salt in a medium bowl and set aside.
  2. In a large bowl, beat the butter and sugar together in a large bowl until combined. Add the egg and vanilla and beat until smooth. Add flour mixture and stir with a wooden spoon until all the flour is incorporated.
  3. Wrap the dough in plastic and gently press it into a disk. Refrigerate for at least an hour (and up to several days).
  4. When you are ready to bake the cookies, preheat the oven to 350° F and line a baking sheet with parchment. On a lightly floured surface, roll out the dough, dusting with more flour if needed, to about 1/4 to 1/8 inch thick. Use a round 1 1/2-inch cookie cutter to stamp out as many cookies as possible and reroll the scraps as necessary. Bake for 7 to 9 minutes or until the tops have set and no longer look wet. Transfer to a wire rack and let cool completely.
  5. Meanwhile make the filling: In a large bowl beat together butter and shortening until combined. Add 2 cups powdered sugar and beat for several minutes until smooth. Add the vanilla extract and seeds and mix until incorporated.
  6. Transfer about half the filling to a small bowl -- this is your booze-free filling. Add the bourbon and 1/3 cup powdered sugar to the remaining filling and beat until combined - this is your booze filling.
  7. Use an offset spatula to spread a small amount of frosting on the bottom side of half of the cookies. Place the remaining cookies on top and gently squeeze each sandwich together to spread the filling to the edges. Filled cookies can be stored in an airtight container in the fridge for several days.

See what other Food52ers are saying.

  • Michael
  • candice boese
    candice boese
  • Amber Bernstein
    Amber Bernstein
  • Ann Marie Noone
    Ann Marie Noone
I was born and raised in Seattle. I moved to New York in 2004, and it has been a love/hate relationship ever since. I moved to Brooklyn in 2010. I have no idea what took me so long. Brooklyn is filled with awesomeness. I love all things made with butter, drinking bourbon, and wearing leggings. I do not own a Kitchen Aid mixer (because I haven’t gotten married yet) or have one single drawer in my kitchen (the joys of apartment life) and my counter can’t accommodate a rolling pin without hitting the stove. Yet, somehow baked goods and other kitchen treats make it out alive to butter y’all up. Please email me at [email protected].

7 Reviews

Samantha R. December 22, 2022
These cookies came out GREAT!

A few things… I weighed each cookie to 35g on a scale to make sure they were uniform for my sandwiches. I used a 2.5 inch round circle “biscuit” cutter and be careful when adding flour to the recipe for rolling, you don’t want dry and cracked cookies.

For the frosting, I used vanilla bean PASTE as my extract and “scrapped vanilla bean” together. So no extract and no bean. Also, I did not create 2 separate frostings for non-alcoholic. In the grad scheme of things, each cookie doesn’t have that much bourbon. Since I did the whole frosting with alcohol, I used a full tablespoon but start with some and add more to YOUR desired taste! Be sure to add a small touch more powdered sugar if you add a good amount more of bourbon to keep your buttercream stiff. I put the frosting into a piping bag with a circle round tip and filled the cookies.

I can’t say enough good stuff about these cookies, light and airy cookie because of the sifting and a light and fluffy filling in the frosting. 5 STARS!!!
Samantha R. December 22, 2022
Michael December 17, 2018
I made these cookies today for a work event tomorrow, so fun to make. They are delicious, like really delicious! I did not split the filling in two, I made the total filling with the bourbon.

Two recommendations: I like bourbon, my coworkers like bourbon...2 teaspoons did not pack a bourbon punch, I put in a total of 8 teaspoons of bourbon.

I found the 1 1/2” diameter cutter too small, next time I will try the 2”.

I will make these again before Christmas.
candice B. April 12, 2015
These were so nice to make! Placing the perfect little circles on the pan and squishing them together later, I could make them all day. And honestly, they taste so amazing!
Amber B. March 22, 2015
I just made these. Fantastic! 5 stars! Dough was easy to work with and tastes great. Just the right texture. The bourbon in the filling is subtle though. So if you want the bourbon to be more readily identifiable, you may want to kick it up a notch.
Ann M. December 18, 2014
Just read your whole comment on shortening, I will substitute butter.
Ann M. December 18, 2014
Can I substitute butter for shortening in the filling?