Gather the ingredients.
1 pint vanilla ice cream
1 cup milk (preferably whole milk)
10 Oreo cookies (or other chocolate sandwich cookie; reserve 2 for garnish)
1 tablespoon chocolate sauce
Place the vanilla ice cream, milk, 8 of the Oreo cookies, and the chocolate sauce in a blender and puree until smooth.
Crush the remaining Oreo cookies by placing them in a zip-top plastic bag and pounding on them a few times with a rolling pin until they crumble.
Pour the milkshakes into 2 tall glasses and top each with the crushed Oreo cookie crumbs. Garnish with a straw.
Serve the shakes immediately and enjoy.
