Shave the chocolate with a vegetable peeler. Set this aside. Chill in the fridge if the kitchen is warm.
Place the shortbread in a ziptop bag and crush with a rolling pin until coarse crumbs are formed. Set this aside.
In a medium mixing bowl, combine the cream cheese, powdered sugar, and vanilla extract. Beat until light and fluffy. Set aside.
In another mixing bowl, whip together the pudding mix and cold milk, beating until well combined and thickened, about 2 minutes.
Assemble the jars
Lay out eight half-pint jars on the work surface. Place ¼ cup cookie crumbs in the bottom of each.
Divide the cream cheese mixture among the 8 jars. Then layer on the pudding. Top with the whipped cream.
Top the whipped cream with shaved chocolate. Serve immediately or chill until ready to serve.
Notes
Nutritional values are approximate and are based on ⅛ of the recipe. Refrigerate leftovers promptly and consume within 2 days. The cookie crumbs will soften the longer it sits.Variations: You can vary the cookie crumbs and pudding to suit your preferences. Pistachio pudding is excellent in this dish!To make an 8-inch square Robert Redford Dessert: Make your own short crust, combine 1 cup flour and ½ cup butter in the bowl of a food processor fitted with a metal blade. Pulse until coarse crumbs are formed. Add 1 tablespoon cold water and pulse until the dough comes together. Press this in the bottom of an 8-inch square pan and bake at 350 for 10 to 12 minutes until golden. Cool completely. Once cool, spread the cream cheese mixture over the crust, sealing to the edge of the pan. Spread the chocolate pudding over that and then top with whipped cream and shaved chocolate. Chill until ready to serve.