Chop the Oreos: Roughly chop your oreos, or add them to a ziplog bag and pound them with a rolling pin until you have a mix of larger chunks and fine crumbs.
14 large oreos
Make Cookie Dough: Melt the butter in a large mixing bowl. Whisk in the sugars, then whisk in the eggs and vanilla until combined. Stir in the dry ingredients (a hand mixer helps here - otherwise you'll need some elbow grease!) making sure to scrape the sides of the bowl to get everything incorporated. Mix in the chocolate chips and oreo pieces last.
14 and 1/2 tbsp salted butter, 3/4 cup brown sugar, packed, 3/4 cup granulated or cane sugar, 2 large eggs, 1 and 1/2 tsp vanilla, 3 cups all-purpose flour, spooned & leveled, 1 tsp baking powder, 1 tsp baking soda, 1/2 tsp salt, 1 and 1/2 cups chocolate chips
Scoop Dough Balls: Scoop the dough into balls that are 85 to 90 grams in size. If you want to stuff cookies with a whole oreo, you'll need 106 grams of dough per cookie.If stuffing, flatten each dough into a thick disc, and place a whole oreo on top. Encase the oreo in the cookie dough, making sure it's sealed up well. Chill: Chill the dough balls in the fridge for at least 1 hour or in the freezer at least 30 minutes. Dough can be chilled in the fridge for up to 48 hours before baking, or frozen in a freezer safe container for up to 2 months. Bake from frozen, at 325℉ for 8-10 minutes (for unstuffed cookies) or 10-13 minutes (for stuffed cookies).
Bake Unstuffed Cookies: Place 5-6 cookies on each baking sheet, and bake one at a time. For slightly crispier outsides and very goody insides, bake for 4 minutes at 400℉, then turn the temp down and bake at 350℉ for 4 to 5 minutes. If you want a more classic cookie, bake at 350℉ for 8 to 10 minutes. Bake Stuffed Cookies: Place 3-4 cookies on each cookie sheet. Bake at 400℉ for 6 minutes, then turn the heat to 350℉ and bake for another 4-5 minutes.Immediately place a round cutter around the outside of each cookie once out of the oven, and swirl the cookie within it to "scoot" them into perfect circles. This helps keep them thicker. Serve & Store: Let cookies cool on the baking sheet on a wire rack for 10-20 minutes, or until cooled just enough to handle. Dig in while they're warm and gooey! (Or let them cool, if you must.) Sprinkle with flaked sea salt if desired. Store cooled, leftover cookies in an airtight container for 3-4 days.
flaked sea salt
Freezing Cookie Dough & Make-Ahead Tips: Cookie dough can be balled, frozen on a sheet pan until solid, then transferred to a freezer bag or airtight container. Freeze for 1-2 months. Bake from frozen, at 325℉ and adding 1-2 mins to the bake time. The cookies may not spread much, but are done when the edges appear and feel just set.