Battles between movie monsters are typically bound to be decided either by the fact that one of them is an unstoppable force while the other is an immovable object. When two forces of this caliber meet it’s usually an epic battle that might never happen, but looks good on paper where it usually stays. These fights are still a lot of fun to think about since it’s worth wondering which combatants would prevail over others, and who would do the most damage on the way out. When it comes to horror monsters there are a lot of tough individuals to think about, especially since the most powerful among them range in size and the type of abilities they possess. In some cases, possession is one of the greatest abilities that a creature has to work with. But in this particular case, possession is kind of an end to a means with one of the characters, as Pumpkinhead is a demon that’s brought to life when one makes a bargain with the backwoods witch that raises the demon from its resting place.
There’s no telling how old the demon is since it could be an ancient, timeless creature that was there when the world was still being formed, or it could be some damned soul that was cursed to be raised again and again as a tool of vengeance. The point of Pumpkinhead though is that there’s nothing to pity, other than the unwitting individual that pays the witch’s price for raising it. Once raised from the swamps, the demon doesn’t stop until its task is finished, or until the one that it’s connected to is slain. Those that watched the first movie should understand that this is one of the main weaknesses of the creature, that it’s bound to the human that desires revenge. So long as that human is alive the demon can’t be harmed, as it kind of embodies the rage, hurt, and pain that the individual was feeling when they asked for this act of vengeance.
On the other end is the Creeper from Jeepers Creepers, who’s a bit more intelligent no doubt since he uses weapons, drives around looking for victims, and has been around since biblical times. That’s a long time obviously, but the thing is that this creature only gets to feed on humans and replenish itself if needed, every 23 years, since during that time, once it’s fed or been defeated, as has happened, it will go dormant for until it’s time to wake and be a nuisance again. At this point, both creatures have had a few movies, but the first has been the best by far since while their initial movies didn’t tell everything, they interested people enough to ask more about the creatures. Throwing them into a death match however feels as though it would favor just one of them, and that’s Pumpkinhead. Without knowing anything about each other, it feels that the demon would hold the upper hand since the Creeper is vulnerable, and can be harmed. The fact that it replenishes itself by eating and stealing parts from human bodies means that if the demon were to tear it apart, the Creeper would have to be near another body to procure the parts it needed, or would have to try and see if he could dismember Pumpkinhead, which is a scary thought.
In terms of strength, Pumpkinhead has been impressive enough since it can lift fully-grown adults with ease, and it can take an alarming amount of damage that would be a serious hindrance to the Creeper. But the Creeper isn’t a weakling either, since he’s survived after being shot, having a javelin punched through his skull, and many other injuries that might not have killed other movie monsters, but would have slowed them down at least. His strength is impressive since the Creeper can also lift adults into the air effortlessly, but there is one advantage he has, and that’s the fact that he can fly. While his weaponry probably wouldn’t do anything to Pumpkinhead, staying out of the demon’s considerable reach would keep the Creeper safe for a while. But the moment that the two came close enough to brawl, it feels accurate to state that the demon would rend the Creeper limb from limb without hesitation.
It wouldn’t be an easy battle by any means, since the Creeper is insanely tough as well. But the fact is that Pumpkinhead could do more permanent damage to the Creeper than the Creeper could do to the demon. If the Creeper ever figured out that the demon was connected to a human, then the tables would turn in a big way since a normal human is no match for the Creeper. But between these two creatures, there’s not much doubt that the victory would go to Pumpkinhead.