Begin by brewing a shot of high-quality espresso. Allow it to cool to room temperature, then place it in the refrigerator for at least 30 minutes.

In a cocktail shaker, combine the chilled espresso with chocolate syrup and a handful of ice cubes. Shake vigorously for about 15-20 seconds.

Carefully strain the mixture into two coupe or martini glasses, ensuring an even distribution.

In a mixing bowl, whisk together heavy cream and confectioners' sugar until soft peaks form, about 2-3 minutes. Spoon this whipped cream over the espresso mixture.

Crush a few Oreo cookies finely and sprinkle over the whipped cream in each glass. Optionally, attach half an Oreo to the rim of each glass.