Add whipped cream to a mixer bowl and beat until stiff peaks form. Refrigerate.

Add softened cream cheese to mixer bowl and beat until creamy.

Add powdered sugar and vanilla and mix until combined.

Fold in whipped cream until well combined.

Crush 12 Oreo cookies in the food processor or place in a zip top bag and smash into crumbs with a rolling pin.

Spoon 1 tablespoon of Oreo crumbs into 6 serving glasses or serving dishes.

Fold in remainder of Oreo crumbs into cheesecake mixture.

Spoon cheesecake mixture over Oreo crumbs into serving glasses.

Garnish with a dollop of sweetened whip cream or whipped topping.

Mix 1/2 cup chocolate chips and 1 tablespoon of milk together in a microwave safe bowl.

Microwave for 30 seconds and stir until chocolate is melted and smooth. Repeat in 15 second intervals until chocolate is smooth.

Drizzle over whipped cream and add a whole Oreo cookie for garnish.

Refrigerate for 30 minutes or until ready to serve.