We rarely buy packaged cookies, but when it comes to Oreos, we just can’t help ourselves. Would it be too over-the-top to include our favorite store-bought cookie in a chocolate chip cookie, we wondered? We had to try. We began by simply chopping up Oreos and folding them into cookie dough, but were less than impressed with the results. Then we came up with the idea of deconstructing the Oreos, using their filling in place of some of the butter and sugar, and the chocolate wafers in place of some of the flour. We found that Double Stuf Oreos gave us the right ratio of filling and cookie. We then added even more Oreos into the finished dough and, of course, some chocolate chips, just to gild the lily.
One note: We highly recommend you use Oreo brand cookies — we tried other chocolate sandwich cookies and didn’t like how any of the results tasted.
Preheat the oven to 350 degrees. Adjust the racks so they divide the oven into thirds. Line 2 baking sheets with parchment paper.
Twist open 13 Oreos and scrape the filling into a small bowl.
In a food processor, grind the separated chocolate wafers until fine; alternatively, put them in a plastic bag and crush them with a rolling pin. Transfer to a medium bowl. Add the flour, baking soda, and salt and whisk to combine.
Chop the remaining 8 Oreos into large chunks.
Put the Oreo filling in a stand mixer fitted with the paddle attachment. Add the butter and brown sugar and mix on medium speed until smooth and well blended, about 1 minute. Add the egg and vanilla and mix until completely combined. Scrape the sides of the bowl with a spatula. Add the flour mixture and mix on low speed until just combined, scraping the bowl if necessary to incorporate the dry ingredients. Add the chocolate chips and mix on low speed until evenly distributed. Remove the bowl from the mixer and gently fold in the Oreo chunks with a spatula. The dough should be smooth, dense, and somewhat pliable.
Using a small ice-cream scoop or tablespoon measure, drop well-rounded balls of dough onto the prepared baking sheets about 2 inches apart.
Bake for 10 to 12 minutes, rotating the baking sheets halfway through the baking time, until the centers look dry but are still soft.
When cool enough to handle, transfer to wire racks to cool completely. Stored in an airtight container at room temperature, the cookies will keep for to 2 to 3 days.