Combine sugar, cocoa, cornstarch and salt in a large sauce pan. Whisk in the milk and cream until smooth. Add chocolate chips and bring to a simmer over medium heat, whisking occasionally.
Reduce heat to medium low and cook, whisking constantly until mixture is thickened and large bubbles appear on the surface. Remove saucepan from heat and stir in vanilla.
Transfer pudding to a heat proof bowl and immediately press a layer of plastic wrap over the entire surface. This will prevent a skim from forming on the top. Allow to cool for about an hour, then store in refrigerator for 4 hours or until completely chilled.
Remove chilled pudding from refrigerator. Take a little more than half of the pudding and divide it evenly among 4 individual serving dishes. Cover the surface of the pudding with a layer of chocolate wafers.
In a medium bowl, using an electric mixer, whip just 1 cup of the cream with 3 Tablespoons of confectioners sugar, until you reach soft peaks. Add the whipped cream to the remaining chocolate pudding, folding it in with a spatula until combined. (Save the bowl you whipped the cream in. It will be used again in the next step.) Divide the creamy chocolate mixture evenly among the individual serving dishes. Spoon it over the cookie layer, insuring the cookie pieces are completely covered. Top the creamy chocolate layer with another chocolate wafer.
In the same medium bowl that you used to whip the cream, whip the remaining 1 cup of cream with the remaining 3 Tablespoons of confectioner's sugar and desired amount of food coloring. Whip this mixture to soft peaks if you want a soft dollop for your topping. Whip to stiff peaks if you'd like to pipe your topping.
Top each serving with the minty whipped cream, completely covering the cookie. Refrigerate for four hours or overnight.
At serving time, garnish with chocolate shavings or mini chocolate chips and a fresh mint leaf.
*I used Nabisco's Famous Chocolate Wafers. You can generally find them in the cookie aisle at the grocery store. They are almost always merchandised on the top shelf in my stores. If you can't find them, you can use chocolate sandwich cookies (like Oreos) and just crush them up (filling and all) in a food processor or by hand until you have crumbs. It won't be exactly the same, but it will still be good!
*You may need more or less wafers depending upon your serving dish. You'll need to use enough to cover the pudding layer.
*Wishing there were more cookie layers in your parfait? Go ahead and add them. Just make sure each layer is fully covered on the top and bottom with your pudding mixtures so that cookies have the opportunity to soften.
*Be sure to use peppermint extract in your whipped cream unless you prefer the taste of spearmint. It will be labeled as, "peppermint." "Mint" extract will taste like spearmint. I only used a 1/2 teaspoon. If you like a stronger flavor, add 1/4 teaspoon more. Just be careful, the flavor can be overwhelming if you use too much.
*If you want to add more peppermint flavor to the dessert, you could add 1/4 teaspoon of the extract to either or both of the chocolate pudding layers. I enjoyed having the minty whipped cream be an accent to the chocolate pudding rather than having the entire dessert be minty.
*Because of the refrigeration time, you'll need to plan ahead. Make it the day before you want to serve it. You can even make the pudding base 2 days before you want to serve it. I wouldn't make the whipped cream portion or layer the dessert until the day before you want to serve it.
Base pudding recipe adapted from Cook's Illustrated Easy Chocolate Pudding, from their special edition, Cook's Illustrated
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