Bourbon Molasses Cookies with Bourbon Buttercream (a.k.a the “Drunken Debbie”)

Bourbon Molasses Cookies with Bourbon Italian Meringue Buttercream

Last weekend, my friend Soffia and I competed in the Brooklyn Cookie Takedown, a cookie competition held at the Bell House in Gowanus, Brooklyn.  To compete, all you have to do is bake 250 cookies, and show up to the venue and hand them out. Not too bad, right? Um…yea – easy, except that it’s 250 cookies (think 20 dozen cookies!).  These were to be made in my tiny, tiny kitchen that lacks a stand up mixer. That’s right people, everything you’ve seen on this site to date is made with the use of my handy-dandy (pun intended) handheld mixer. 

Bourbon Molasses Cookies

Bourbon Molasses Cookies

Because the competition was held the week after Thanksgiving, and both Soffia and I were traveling for the holiday, we had to come up with the recipe remotely.  We collaborated over e-mail, shared recipe ideas, and messengered cookies to each other’s offices so we could taste test (only in New York would you pay someone to deliver a paper bag full of cookies on-demand, right?).  We used our colleagues as guinea pigs taste testers, and they were happy enough to try more than 5 different types of cookies over the course of a week. (I only got a few grumblings for being a cookie pusher, no big deal.)

We decided we wanted to do a boozy theme (because what’s better than baking with bourbon?), and picked an alcohol-infused version of Bon Appétit’s Chewy Molasses Cookies.  But while the cookie was incredibly tasty (if I do say so myself), we didn’t know if it was show-stopping.  Soffia suggested we sandwich them with an Italian Meringue Bourbon Buttercream, and I knew immediately that they would be a winner.

Bourbon Molasses Cookies

Bourbon Molasses Cookies

While I knew they’d be delicious, I did have concerns with the recipe: (1) the amount of cookies we needed to bake just doubled to 500! and (2) anytime I’ve tried to make a meringue buttercream I’ve failed miserably and sobbed into the curdled goo. But I wanted to win, so we agreed to make the sandwich cookies, and Soffia very generously offered to make the buttercream.  Thanks to my clever friend David, we named our cookie the “Drunken Debbie”, since it was sort of like a grown up version of a Little Debbie, but slightly alcoholic and significantly more delicious.

Bourbon Molasses Cookies

The competition was on Sunday, and Saturday happened to be a whirlwind of events: my parents were in town for brunch, and a friend’s afternoon birthday party soon became an all-day event, so by the time I got back to my apartment it was well after 10pm. Slightly tipsy (it seemed fitting since we were making boozy cookies), I set about making my share, some 360+. After a few incidents – a minor burn and a tray of cookies falling onto the bottom of the oven, causing the entire apartment to fill with smoke and our smoke alarm going off at 1am – I successfully baked 30 dozen, bourbon molasses cookies. I slept well that night, that’s for sure.

Bourbon Italian Meringue Buttercream

Bourbon Italian Meringue Buttercream

Bourbon Italian Meringue Buttercream

The next morning, Soffia came over to ice and assemble the cookies.  She brought the 4 pounds of buttercream she had made, which had been refrigerated over night and just needed a little whip from a mixer to get it up to room temperature and return it to it’s light and fluffy consistency.  Problem was, I only had the hand held mixer.  As soon as Soffia started mixing the buttercream, it immediately separated and looked like the curdled mess I was used to.  We had hope though, and my resourceful boyfriend, Jordan, went to a friend’s apartment to borrow her KitchenAid as a last ditch effort.  It really felt like we were in the finale of Top Chef, pulling out all the stops. Luckily, after a few minutes in a proper mixer, the icing came back together, and it was everything we wanted it to be: boozy, fluffy, sweet and absolutely delicious.

Bourbon Molasses Cookies with Bourbon Italian Meringue Buttercream

Bourbon Molasses Cookies with Bourbon Italian Meringue Buttercream

Bourbon Molasses Cookies with Bourbon Italian Meringue Buttercream

Bourbon Molasses Cookies with Bourbon Italian Meringue Buttercream

We made a mad rush to finish sandwiching all of the cookies, packed them up and raced to the event, where we arrived with 5 minutes to spare.  There were 30 teams at the event, with cookies ranging from shortbreads, to chocolate chip, to a clever takes on s’mores. Over 250 people attended the competition, and everyone voted for their favorite.  I am super excited to say that our Drunken Debbie won 1st place people’s choice, with almost 50 votes!!! All the hard work and collaboration paid off, we were cookie champions!!

Win during the Brooklyn Cookie Takedown

Courtesy: David Martinez

The best part: the 1st place prize was a KitchenAid Stand Mixer!!!! Everything comes full circle, huh? Soffia said it was fate, and since she already had her own, I am now happy to say that I am the proud owner of a beautiful, light blue KitchenAid Stand Mixer.  I can’t wait for all the things I’m going to make with this sexy, sexy piece of equipment.

Bourbon Molasses Cookies with Bourbon Italian Meringue Buttercream

Bourbon Molasses Cookies with Bourbon Buttercream (a.k.a the Drunken Debbie)

  • Servings: ~2 dozen sandwich cookies, or ~4 dozen standalone cookies
  • Difficulty: medium
  • Print

Note: This recipe is relatively involved, after all we needed to step up our game since it was a competition.  While the icing really takes this cookie to the next level, I think the cookies are perfectly delicious on their own, and are worth making even if you don’t have time for the meringue buttercream. The buttercream for the recipe will make more than you need, but it freezes well (for up to a month), so store it until you’re ready for your next bourbon baking concoction.  

Cookies adapted from Bon Appétit; Buttercream from my friend Soffia Yen

For the cookies:

INGREDIENTS

  • 2 cups all-purpose flour
  • 2 teaspoons baking soda
  • 2 teaspoons ground cinnamon
  • 1 teaspoon ground ginger
  • 1/2 teaspoon ground cloves
  • 1/4 teaspoon ground all-spice
  • 1/2 teaspoon kosher salt
  • 1/2 cup (1 stick) butter
  • 1/3 cup granulated sugar
  • 1/3 cup unsulphured, dark molasses
  • 1/4 cup (packed) light brown sugar
  • 1 large egg
  • 1 tablespoon bourbon
  • Course sanding or turbinado sugar (for rolling)

RECIPE

  1. Pre-heat oven to 350° F. Line two baking sheets with parchment paper.
  2. In a medium bowl, whisk together the flour, baking soda, cinnamon, ginger, cloves, all-spice and salt.  Set aside.
  3. In a small saucepan, heat the butter over medium heat until it has browned and smells slightly nutty.  Be sure not to overcook as the butter may burn.  Pour the butter into a large, heat-proof bowl and allow to cool.
  4. Once browned butter is cool, add the sugar, brown sugar, molasses, egg and bourbon, and whisk to combine.  Mix in dry ingredients just until combined.
  5. Place sanding sugar in a shallow bowl.  Scoop out dough by rounded teaspoon, and roll into balls (if dough is too sticky, refrigerate for up to 20 minutes).  Roll in the sugar, and place on the cookie sheets.
  6. Bake for 7-8 minutes, until cookies are puffed, cracked and lightly browned just around the edges – be sure not to overcook as they will lose their chewiness.  Transfer to a wire rack to cool.
  7. If making a sandwich, pipe or spread with an offset spatula 1 teaspoon of icing onto half of the cookies. Top the cookie and icing with a similar sized cookie and press slightly down to create a sandwich.
  8. Cookies will store for 3 days in an air-tight container at room temperature.

For the Bourbon Italian Meringue Buttercream

INGREDIENTS:

  • 3/4 cups granulated sugar, 2 tablespoons reserved
  • 3 large egg whites
  • 2 sticks unsalted butter, cubed and chilled
  • 3 tablespoons bourbon
  • Special Equipment: candy thermometer

RECIPE:

  1. In a small saucepan whisk 3/4 cups (minus 2 tablespoons) sugar and 1/3 cup water. Bring to a boil over medium-high heat, and continue to boil until it reaches 235° on a candy thermometer (soft-ball stage). Use a wet pastry brush to keep sides of pot clean while sugar cooks.
  2. While the syrup is boiling, place the egg whites and reserved 2 tablespoons of sugar in the bowl of a standing mixer fitted with the whisk attachment.  Beat on low speed until foamy.
  3. With the mixer on medium speed, add the soft-ball sugar to the foamy egg whites in a slow and steady stream.  While pouring, avoid hitting the whisk attachment or pouring down the side of the bowl, you want the hot syrup to be added directly to the egg whites.  Raise the speed to high, and be until mixture is no longer steaming, about 3 minutes.  Meringue should look bright white, shiny and voluminous.
  4. Add the butter, bit by bit, beating until spreadable, about 3 to 5 minutes.  Beat in the bourbon, a tablespoon at a time, until mixture is light and fluffy.  If buttercream curdles, keep beating until smooth.

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17 thoughts on “Bourbon Molasses Cookies with Bourbon Buttercream (a.k.a the “Drunken Debbie”)

  1. Congratulations Cassie! I won in 2011 and 2012, so welcome to the Brooklyn Cookie Takedown winners circle! Also I don’t know how you did it all without a stand mixer but you have one now, so my hat is tipped off to you. If I hadn’t been working, I’d be there and for sure anything with bourbon would have gotten my vote.

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  3. I am so excited to make thsee! Is there a measure of bourbon in the cookies themselves? I think it is omitted from the ingredients list, but it is in the instructions.

  4. These cookies are unreal! The flavor is so complex, with molasses, spiciness and a wee bit of booze coming through, all in a tender cookie with a satisfying crunch of sugar on the outside. The buttercream is just incredible. Making again this week, cuz they’re almost gone!

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    • They should last for 24 hours if stored in a cool, dry air-tight container. They went so fast that I didnt have any leftovers! But I made the icing for cupcakes and it held up well overnight. Hope you enjoy them!

      • Finished the frosting and assembled the cookies. They are adorable. You’re right. The frosting makes a LOT! I thought I would not be able to move the frosting from a cottage cheese state to a smooth texture. I really wanted it more of a light whipped look like what i see here, however I am happy with the results. Its a heavier frosting but O-M-G the flavor is OUT OF THIS WORLD. I need to find something to do with the left over frosting. I’m worried I may sit down with the bowl and eat it by itself. (disclaimer-that wont happen but doesn’t mean I don’t want too). Thanks for the recipe and the advice.

      • Im so glad you like them! Were you able to get the icing to whip? If you keep mixing, eventually it will come together. You can also use the trick of taking 1/4 cup of the curdled icing, stick it in the microwave for 20 seconds and then adding it back to the icing and mix for a couple minutes. I don’t know why, but it always does the trick. I made ginger cupcakes with the leftover icing, they were delicious! It would also be good with chocolage or vanilla cupcakes!

  7. Wow oh wow! I entered your recipe into my church’s cookie contest and won. These are so scrumptious. Thank you for a wonderful recipe.

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