Special equipment: a 6-cup jumbo muffin pan
Whip together the heavy cream and confectioners' sugar in a large bowl with an electric mixer on medium-high speed until stiff peaks form, about 2 minutes. Fold in the pudding with a rubber spatula until well combined.
Cut 6 squares of plastic wrap large enough so that each cup of a 6-cup jumbo muffin pan is completely lined with a slight overhang at the top.
Spread 1 heaping tablespoon of the pudding mixture over the bottom of a lined muffin cup. Break up 2 cookies and fit them into an even layer over the pudding. Repeat twice with the pudding and cookies until the muffin cup is full, ending with a cookie layer on top. Fill the remaining 5 muffin cups with the pudding and cookies, layering in the same manner. Cover each cup with the overhanging plastic wrap. Refrigerate for at least 8 hours and up to 12. Reserve the remaining 6 cookies for garnish.
When ready to serve, unwrap each cake and invert the muffin pan onto a large platter or cutting board all at once. Remove the plastic wrap. Transfer the individual cakes to serving plates. Crush the reserved cookies and sprinkle some on top of each cake, then drizzle with the chocolate syrup.
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