Preheat oven to 375 degrees.
Chop 16 Holiday Oreos into pieces. I keep the pieces pretty chunky. Set aside.
Cream the butter and sugars together with a mixer (stand or hand) on medium speed until light and fluffy.
Beat in the eggs and vanilla until combined. Add in the flour, cocoa powder, baking soda, and salt. Slowly mix it all together until combined. Add the milk and mix until it is just combined. Stir in the chopped Holiday Oreos and chocolate chips.
Using a cookie scoop or spoon, scoop cookie dough onto baking sheet. Make them as big or as little as you'd like. Bake at 375 for 9-10 minutes.
After removing from oven, let the cookies stay on the cookie pan for a couple extra minutes. Remove cookies and cool on cooling rack.