Preheat broiler to high and place an oven rack about 5 inches from the heat source. Line a baking sheet with foil and mist with nonstick cooking spray. Stack 8 tortillas on a cutting board and use a sharp paring knife to trim away some of top leaving a 1 inch stem so tortillas are shaped like a pumpkin. Repeat with remaining 8 tortillas. Use a knife to cut two triangles for eyes and a crescent for a mouth into 8 tortillas.
Warm 1 tsp oil in a large skillet over medium heat. Add a tortilla without eyes and mouth, sprinkle with 1/2 cup of cheese. Cover with cut out tortilla cook until underside is golden about 1-2 minutes, slide onto a baking sheet, and repeat to make three more quesadillas.
Place baking sheet under broiler until tops are golden. Slide onto a serving platter and loosely tent with foil to keep warm. repeat with remaining tortillas and cheese. Serve immediately.