Using a sharp paring knife, cut pumpkin faces into 5 tortillas. [pro tip: freeze your tortillas first; they're easier to slice this way!] Using excess, cut 5 small square pieces for the "stem."
Spray the inside of a large fry pan with nonstick cooking spray. Set to medium-low heat.
Place one uncut tortilla on your fry pan. Top with cheese and pumpkin-cut tortilla. Fry 2-3 minutes, flipping once halfway through.
Place quesadillas on serving plates and tuck the tortilla "stem" underneath.
Serve warm with sour cream, salsa and hot sauce, if desired.