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 steer 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.
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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, divided
1 vanilla bean, seeds scraped
1 teaspoon vanilla extract
2 teaspoons bourbon
Sift together the flour, cocoa powder, baking soda, baking powder, espresso powder, and salt in a medium bowl and set aside.
In a large bowl, beat the butter and sugar together until combined, then add the egg and the vanilla and beat until smooth. Add the flour mixture and stir with a wooden spoon until all of the flour is incorporated. Wrap the dough in plastic and gently press it into a disk. Refrigerate it for at least an hour and up to several days.
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, until it is 1/4 to 1/8 inch thick. Use a round 1 1/2-inch cookie cutter to stamp out as many cookies as possible, then reroll the scraps as necessary. You should get about 48 cookies, which will make two dozen sandwiches.
Bake for seven to nine minutes, or until the tops have set and no longer look wet. Transfer the cookies to a wire rack and let them cool completely.
Meanwhile, make the filliing. In a large bowl, beat together butter and shortening until combined. Add two cups of powdered sugar and beat for several minutes until smooth. Add the vanilla extract and seeds and mix until incorporated.
Transfer about half the filling to a small bowl — reserve this as your booze-free filling. Add the bourbon and the remaining 1/3 cup of powdered sugar to the rest of the filling and beat until combined — this is your boozy filling.
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.
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