Preheat the oven to 350℉ (177℃). Line baking sheet pans with silicone baking mats or parchment paper.
In the bowl of a stand mixer fitted with a paddle attachment or a large bowl with an electric hand mixer, cream together the unsalted butter, brown sugar, and granulated sugar until well combined. Add in the eggs and vanilla extract and mix until smooth.
Add in the all-purpose flour, baking soda, salt, and mix on low speed until the cookie dough forms. Fold in the Oreo cookie crumbs, roughly chopped Oreo cookies, and semisweet chocolate chips until they are well dispersed throughout the cookie dough.
Portion the cookie dough using a large cookie scoop (3 tablespoons). Press additional Oreo cookie pieces and semisweet chocolate chips into the cookie dough, if desired.
Place the cookie dough balls onto the prepared baking sheet pans allowing room for spreading. Bake the cookies for about 12 minutes until the edges are golden-brown and the centers are slightly underdone. Cool the cookies on the pan for 2 minutes and then transfer to a wire rack to cool completely.