Place milk, ice cream, vanilla extract, and crushed oreo cookies into the milkshake canister or blender. If using a milkshake canister, briefly mash mixture together with a fork, then blend in the milkshake maker.
Blend until achieving the thickness you enjoy best.
Pour your thick and creamy homemade oreo milkshake mixture into 2 cups. Top with a few crushed oreo crumbs, whipped topping, chocolate syrup, and a cherry.