In a heavy saucepan over medium-high heat, combine the sugar with 1/4 cup of water.
Combine the cookie crumbs and chocolate chunks in a large resealable bag.
Using a large round ice cream scoop, scoop out a ball of ice cream and leave it in the scoop. Poke a hole in the center of the scoop with a handle of a wooden spoon and put a cherry into the hole. Cover the hole with a bit of ice cream and put the scoop of ice cream into the bag of cookies and chocolate pieces. Shake around pressing gently to completely coat the ice cream. Put the scoop on a tray and freeze for 30 minutes. Repeat the process with remaining ingredients.