Hollow out medium round pumpkin from the bottom. Carve half-circle mouth with a tooth, 2 half-circle eyes with pupils and triangle nose. For eyes, push in inner piece (don't remove). Then, etch away skin on pupils and tooth with linoleum cutter. Use awl to poke holes about 1½" apart across top and sides of pumpkin. Push lollipops (Orange Sassy Suckers, $25 for 100; candywarehouse.com) into holes to create hair.