Place the KitchenAid ice cream bowl in the freezer and freeze for 15-24 hours before making this recipe.
Place chocolate in a microwave safe bowl and melt in the microwave starting with one minute and then stirring after every 30 seconds until melted.
Add 1/3 cup unsweetened cocoa powder to the melted chocolate. Stir.
Add 1 cup heavy cream and 1/2 cup milk and whisk until smooth.
Set chocolate mixture aside.
In KitchenAid mixer, whisk eggs on speed high (10) until light and fluffy (about 1-2 minutes).
Turn the mixer speed down to 8, slowly add sugar and whisk for about 1 minute.
Switch out the whisk for flat beater.
With the mixer on 'STIR', add 1 cup heavy cream and vanilla.
Once blended, gradually add chocolate mixture and 3/4 cup crushed Oreo pieces.
Once blended, cover the mixing bowl with plastic wrap and refrigerate the ice cream batter for at least 2 hours.
Attach the dasher adapter with short tab around pin and lock firmly into place. Place frozen ice cream bowl onto mixer and insert dasher. Lock mixer head down and engage dasher on 'STIR'.
Slowly pour ice cream batter into bowl with dasher moving. Stir for 25-30 minutes.
Transfer soft-ice cream to an airtight container, sprinkle on a few more Oreo crumbles, and freeze for 24 hours.
Enjoy!