Coarsely crush 8 chocolate sandwich cookies and 8 chocolate chip cookies into small pieces. Crush the 2 chocolate sandwich cookies until they are finely chopped in a small bowl. Keep the larger cookie crumbs and finely crushed cookie crumbs in separate bowls and set them aside.
Place parchment paper in loaf pan. (With extra hanging over the sides to cover the ice cream with later)
Pour the sweetened condensed milk into a large bowl. Set aside.
Pour the heavy whipping cream into a mixing bowl. Using your whisk attachment on your mixer, whisk the heavy whipping cream until stiff peaks form (about three minutes).
Gently fold in about a cup of the heavy whipping cream into the sweetened condensed milk.
Add in the remaining heavy whipping cream and the finely crushed cookie crumbs and gently fold until combined.
Pour half of the cream mixture into your prepared loaf pan. Evenly sprinkle half of the larger cookie pieces over the mixture. Repeat this step with the other half of the mixture and cookie crumbs.
Drag a knife or spatula through the cream mixture to spread out the cookie pieces.
Fold over the parchment paper to cover the top. (I use masking tape to keep it together.)
Freeze six hours.
Ice cream will keep good in freezer for up to two weeks.