Place chocolate sandwich cookies in a plastic sealed bag. Use a rolling pin to finely crush the cookies (alternatively, a food processor may be used). Set aside.

Using a handheld or stand mixer fitted with the paddle attachment beat cream cheese, powdered sugar, and vanilla extract at medium speed until smooth, about 2 to 3 minutes.

With the mixer on low, slowly add heavy whipping cream and then increase speed to medium-high. Beat until the mixture is stiff about 4 to 5 minutes.

Divide mixture in half and placing it in two mixing bowls.

In the first bowl, fold in half of the roughly chopped/crushed cookies (about 1/2 cup). In the second bowl, stir in cocoa powder until thoroughly combined.

Transfer mixtures to two separate pastry bags for assembly.

Using 8-ounce mason jars as containers, add layers of the chocolate cheesecake mixture, cookie cheesecake mixture and finely crushed cookie crumbs as you see fit, finish with any remaining cookie crumbles on top.

Chill parfaits for 2-3 hours before serving. Garnish with whipped cream and chocolate cookie sandwich if desired. Serve cold.