These Double Chocolate Cookies & Cream Cookies are so rich and chocolatey with a brownie-like texture and homemade white and dark chocolate bark studded with Oreo cookies! These deep, dark cookies are made with black cocoa powder to mimic the color and flavor of classic Oreos and they taste just like them except with a soft, chewy and fudgy texture.
First make the cookies & cream bark. Place chopped dark chocolate in a heatproof bowl set over a saucepan with ½ inch of simmering water. Make sure the bowl is large enough that it just rests over the pot and the bottom of the bowl doesn’t touch the water. Stir constantly until completely melted and smooth. See this post for how to temper chocolate if you’d like to go the mile, otherwise just melt it gently and do not over-heat it. Do the same with the white chocolate, being extra careful as white chocolate has a lower melting temperature and can burn easily.
Pour the dark chocolate over a baking tray lined with parchment paper and spread it out so it is between ⅛ inch and ¼ inch thick. Drizzle the white chocolate randomly over top and then swirl it in a bit. Sprinkle chopped Oreos over the chocolate while it is still fluid and then allow it to set in a cool place for about 30 minutes until firm. Once firm and set, chop up the bark into chunks and set aside.
Make the cookie dough. Sift flour, Dutch cocoa, black cocoa, baking soda and salt in a medium bowl and whisk to blend evenly.
Combine butter with both sugars and vanilla in a large bowl and mix for 2-3 minutes using an electric hand mixer on medium speed until smooth, pale and fluffy. You can also use a stand mixer fitted with the paddle attachment or cream by hand with a wide rubber spatula. Stop to scrape down the sides of the bowl a few times during mixing. Add egg and mix until well combined. Add dry ingredients and mix on low until it just begins to incorporate. When most of the flour is incorporated, it will look a bit dry and now you can add the milk. Continue folding the dough until the ingredients are evenly combined. Add about ⅔ of the chopped chocolate Oreo bark and fold it in evenly. Cover the bowl and refrigerate the dough for 1-2 hours.
Use a 1.35-oz cookie scoop to portion dough and then roll into smooth balls. Place them onto prepared baking sheets spacing them 3 inches apart. Press a few more pieces of chocolate bark on top of each ball and bake for 9-11 minutes until puffed and the tops are cracked but they are still soft in the middle. Transfer to a rack and let cookies cool on trays for 3 minutes before transferring individually to the rack to finish cooling.