Finely crush 10 Oreos and press them firmly into the bottom of an 8 x 8-inch baking dish to form the crust.
Place the chocolate chips in a microwave-safe bowl. Microwave on high for 30 seconds, stir, then repeat in 30-second intervals until fully melted.
Cube the cream cheese and add it to the melted chocolate. Sprinkle 1 tbsp of instant coffee over the top and stir until the mixture is smooth and combined. Set aside.
In a large bowl or stand mixer, add the heavy whipping cream. Sprinkle the remaining 2 tbsp of instant coffee and powdered sugar over it. Stir gently, then beat until stiff peaks form.
Stir ½ cup of the whipped cream into the chocolate and cream cheese mixture to lighten it. Fold in an additional cup of whipped cream until just combined.
Spread the chocolate cream cheese mixture over the Oreo crust, forming an even layer.
Arrange 16 whole Oreos on top of the chocolate cream cheese layer.
Spread the remaining coffee whipped cream over the Oreos.
Crush 5-10 of the remaining Oreos with your hands and sprinkle them over the whipped cream layer.
Cover loosely with plastic wrap and refrigerate for at least 8 hours or overnight. When ready to serve, let it sit at room temperature for 10 minutes for easier cutting.