Begin by pouring 2 cups of heavy whipping cream into a large mixing bowl. Using an electric mixer, whip the cream on medium-high speed until soft peaks begin to form, about 2-3 minutes. Gradually add ¾ cup of powdered sugar and 1 teaspoon of vanilla extract, then continue to whip until you achieve firm peaks, approximately another 2 minutes. Set aside the luscious whipped cream for later use in the Chocolate Oreo Icebox Cake.

In a microwave-safe bowl, melt 1 cup of semi-sweet chocolate chips in 30-second intervals, stirring in between until smooth. Allow it to cool slightly while you beat 8 ounces of softened cream cheese in a separate bowl using an electric mixer. Once fluffy, add the remaining ¾ cup of powdered sugar, 1 teaspoon of espresso powder, and a pinch of salt. Mix until well combined, then pour in the melted chocolate and blend until fully integrated.

Gently fold half of the whipped cream into the chocolate cheesecake mixture using a spatula, being careful not to deflate the cream. Once incorporated, add the remaining whipped cream, folding until the mixture is smooth and creamy.

In a 9x13 inch dish, create the first layer by arranging a single layer of Oreos along the bottom. Spoon half of the chocolate cheesecake mixture over the Oreos, spreading it evenly. Next, add half of the remaining whipped cream over the cheesecake mixture, smoothing it out gently. Repeat this layering process.

Cover the assembled Chocolate Oreo Icebox Cake tightly with plastic wrap. Place it in the refrigerator and chill for at least 4-5 hours; overnight is ideal.