Combine the finely crushed Oreos, melted butter, and milk in a bowl. Stir until the mixture is soft and moldable, resembling a thick dough that holds together nicely.

Lay a sheet of plastic wrap on a flat surface. Press the Oreo mixture into an 8x10-inch rectangle, ensuring it's evenly spread.

In another bowl, beat the softened cream cheese, powdered sugar, and vanilla extract until smooth and creamy.

Gently fold in the whipped heavy cream until just combined.

Carefully spread the cream cheese filling evenly over the Oreo base, leaving a small border around the edges.

Using the plastic wrap, roll the Oreo base tightly into a sushi-style roll.

Wrap the rolled sushi in the plastic wrap and refrigerate for at least 1 hour.

Once chilled, drizzle with chocolate syrup and sprinkle extra crushed Oreos on top. Slice into bite-sized pieces and serve.