Place two tall milkshake glasses in the freezer to chill while making the milkshakes.TIP: If you want to chill a glass quickly, fill the glass with crushed ice and soda water while preparing your milkshake!
Blend together ice cream, milk, and 10 Oreo cookies.TIP: Use Cookies and Cream or chocolate ice cream for a more chocolatey Oreo milkshake. You can add 1 cup of ice to the ingredients for added thickness and also cut the richness a little. Less milk will also make a thicker milkshake. You can also swap in a lower fat milk or even frozen yogurt to reduce the calories. A lower fat milk may make this a little thinner.
Drizzle chocolate syrup on the inside of each chilled glass and/or along the rim.TIP: Use hot fudge sauce for a thicker drizzle on the inside of the glasses.
Divide milkshake mixture between the two glasses.
Top with whipped cream, more chocolate syrup, crushed Oreos, and/or a whole Oreo.