Using a blender, working in batches, puree the ice cream, chocolate milk and bananas. Pour into a large pitcher or vase.
Cut the Fruit Roll-Up into a 5-inch circle and wrap around the doughnut hole, cutting slits as necessary to cover the doughnut smoothly. Cut a long, thin strip off the licorice twist to form a "stem"; poke the stem into the doughnut "cherry."
Top the milkshake with the whipped cream and place the cherry on top.