Preheat the oven to 350 degrees F. Spray a 2 1/2-quart ovenproof bowl with cooking spray. Put paper liners in 3 cups of a muffin pan. Prepare a chocolate cake mix as directed. Fill the liners two-thirds of the way, then pour the rest into the prepared bowl.
Bake the cupcakes and bowl cake until a toothpick inserted into the centers comes out clean, about 18 minutes for the cupcakes and 50 minutes for the bowl cake. Let cool. Remove the bowl cake and peel off the liners; freeze 20 minutes.
Put the bowl cake upright on a cake board or plate. Carve out the middle, about 1 inch from the edge, with a paring knife to make room for the "guacamole."
Cover the top and sides of the bowl cake with chocolate frosting.
Pat ground chocolate sandwich cookies over the frosting to cover. Invert the cake onto another cake board or plate.
Frost the bottom of the bowl cake. Trim the cupcake tops to make them level and attach to the bottom of the bowl cake with frosting.
Frost the sides of the cupcakes as shown. Pat cookie crumbs into the frosting to cover completely. Transfer to the freezer.
Mix the ice cream with 14 drops of green food coloring, 8 drops of yellow and 2 drops of red until it turns guacamole green. Stir in the candied cherries.
Invert the cake so it's bowl-side up. Pat any loose crumbs into place, then fill with the ice cream. Freeze at least 1 hour. Serve with cinnamon-sugar pita chips.