Step 1: Grab your blender and make sure it's ready.
Step 2: Carefully add the ice cubes, milk, granulated sugar, and vanilla extract to the blender pitcher.
Step 3: Add the 8 Oreo cookies to the blender.
Step 4: Secure the lid and blend until the mixture is smooth and creamy, with tiny bits of Oreo cookie still visible. Start on a lower setting if needed, then increase to high. You may need to stop and scrape down the sides with a spatula.
Step 5: While the blender is working, grab your favorite tall glass. Drizzle chocolate syrup generously around the inside walls of the glass.
Step 6: Once blended to your desired consistency, pour the Frappuccino mixture into the prepared glass.
Step 7: Pile on the whipped cream.
Step 8: Finish by crumbling or placing extra Oreo cookies on top of the whipped cream.
Step 9: Serve immediately and enjoy!