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Top 10 Pumpkinheads

Happy Halloween, everyone! What’s that? It’s not Halloween anymore? BALDERDASH! HALLOWEEN IS IN MY SOUL! IT CAN BE HALLOWEEN IF I WANT IT TO BE! (harumphs) …Anywho. In the past, I’ve covered all kinds of typically Halloween-y things here. I’ve talked about vampires, I’ve talked about werewolves, I’ve talked about the Frankenstein Monster, I’ve talked about skeletons, the list goes on…but somehow, there’s one staple of Halloween I never managed to touch on. Pumpkins. Jack O’Lanterns. More specifically, Pumpkinheads. The history of why the pumpkin has become the staple squash of autumn, and especially around Halloween, is a long story that I won’t get into here. Suffice it to say, the idea of characters with carved pumpkin craniums is a rather common trope found in all kinds of places. It’s not hard to see why, the visual is just a very interesting one: a glowing, carved Jack O’Lantern atop a more or less human body just has a sort of unsettling vibe to it, and yet can also lead to all kinds of directions to take characters. Some of them are cute, some of them are creepy, and some of them are just plain fun. Before I get into this list, there are three big characters/creatures I need to bring up who will NOT be on the countdown. First, there’s the titular monster from the horror film “Pumpkinhead,” and the character of Sam from the movie “Trick ‘r’ Treat.” They are not included here simply because I have not seen those movies, and therefore do not know much about them. Second, there’s the Great Pumpkin from the Peanuts franchise, and similar characters who are basically just pumpkins rather than specifically having pumpkinheads. Aside from that issue, in the case of the Great Pumpkin, the whole idea of the character is that…well…he may or may not even EXIST, so that makes it a bit hard for him to count on any rubric you name. With that said, hopefully the ten I’ve chosen will be of some interest! If there are any famous pumpkinheads you know and love not found here, chances are good it’s just because I’m not familiar with them. So, without further ado, here are My Top 10 Favorite Pumpkinheads!

10. Pumpkinmon, from Digimon: Ghost Game.

Also called “Pumpmon;” not sure which is the more common or correct name. I should add I am SPECIFICALLY talking about the version that appears in the series “Ghost Game” because…well, to be honest, I’m not a Digimon fan. I don’t know any other versions OF this little rascal EXCEPT the one in this series, which is the only Digimon series I can honestly say I’ve seen and really loved. (Although the ongoing Beatbreak series MIGHT eventually join it as a close second…but I digress.) This show was basically Digimon meets Scooby-Doo, with the main characters solving various creepy mysteries seemingly connected to such supernatural beasties as ghosts, vampires, and zombies…only for it to quickly be revealed the supposed occult goings-on are the results of rogue Digimon running amok. It’s only fitting that, fairly early in the show, this spooky series decided to do a Halloween-themed episode, and featured Pumpkinmon as the central antagonist of the hour. This spooky fellow can summon giant sized pumpkins to attack with in various ways, and turn people into pumpkinheaded thralls under his control. Interestingly, this little gremlin is usually depicted as more “cute” than “creepy,” to my understanding, in other versions of the franchise…but in this series, they managed to make this little monster BOTH. Pumpkinmon at first is downright TERRIFYING, and what he’s doing is quite disturbing - the sound effects and visuals only adding to the horror - but when you find out his true motivations, he honestly becomes a very sympathetic character. We find out his horrible hauntings were essentially just the result of him being lonely and misunderstanding how Halloween works. As a result, an episode that starts off as extremely frightening ends on a surprisingly warm, fuzzy, wholesome note. Despite being one of the earliest entries in the show, it’s still one of my favorite episodes from the series, and while I don’t know how this hobgoblin stacks up in other versions, he’s worthy of placement in the top ten for this appearance alone. Speaking of Hobgoblins…

9. Jack O’Lantern, a.k.a. Mad Jack, from Marvel.

Jack O’Lantern - sometimes called “Mad Jack” - is a somewhat obscure villain from the Marvel universe. He’s faced foes like Ghost Rider and Captain America a few times, but is most well-known (when he’s known at all) for his rivalries with Spider-Man. Multiple people have donned the mask and armor of this spooktacular scoundrel over the years, but most of them have a few things in common…such as their arsenal. Stop me if you’ve heard this one before: Jack uses a hoverboard-esque glider, pumpkin bombs, and gauntlets that blast energy bolts as his primary weapons. Seem familiar? If you’re thinking, “Wow, that’s basically a ripoff of the Green Goblin and the Hobgoblin,” then you’re correct…and what’s interesting is, that’s kind of the point. A lot of people write Jack off as JUST a Diet Goblin, but what I find intriguing about the character is that his similarity to these two villains is a big part of what makes the character in the first place: most versions of Jack depict the character as a cold-blooded mercenary who uses weapons self-consciously similar to the Goblins as a means of committing crimes. Jack doesn’t usually have superhuman abilities, and isn’t typically a hyper-strategic or exceptionally intelligent fellow, but he’s rarely treated as a joke, either: most of the time, Jack is a stone-cold serious crook who WANTS to be one of the “big boys,” but can never quite make it work. Ironically, a few versions of Jack have either teamed-up with or even temporarily BECOME the Hobgoblin, in particular, during the course of their supervillain careers. I love this idea of a villain deliberately inspired by other villains who isn’t necessarily an incompetent loser: left to his own devices, Jack IS a force to be reckoned with, but when you put him up against his predecessors, it becomes quickly clear the power level is off, and that’s what’s fun about it. There have been occasional attempts to rework and revamp this character, usually giving him a supernatural blend (such as the one in the animated series “Ultimate Spider-Man,” where he’s a sentient scarecrow brought to life by Morgan le Fay) or taking him full out into the realm of horror (such as the one in the Agent Venom series, where he’s a disfigured and deranged serial killer who carves people’s faces up like Jack O’Lanterns), but somehow Jack’s creators and handlers tend to keep falling back on him as the pumpkinheaded mercenary. While I definitely like the Goblins a LOT more, I do have a soft spot for this villain, too, and he’s earned some recognition here as a result.

8. The Pumpkin People of Pottsfield, from Over the Garden Wall.

Much like Pumpkinmon from Ghost Game, the People of Pottsfield are characters who start off as EXTREMELY creepy…but by the end of it, suddenly become much more sympathetic and understandable. In the second episode of the animated dark fantasy series “Over the Garden Wall,” our protagonists find themselves stumbling upon a rural community of mysterious folk who live in a little town called Pottsfield…and every single person in Pottsfield has a pumpkin for a head. At first it’s unclear what’s going on in this little town, and whether the pumpkin people are wearing costumes or not…but bit by bit, we eventually learn the truth. That truth is both sad and honestly REALLY disturbing. You see, the People of Pottsfield AREN’T men and women with ACTUAL pumpkinheads technically speaking…but instead are living corpses, reduced to naught but bones, who wear the pumpkins and scarecrow-like outfits as protection, to give themselves some semblance of a body again. The reason they are this way is because of the main antagonist of the series, a devil-like creature simply called “The Beast.” It’s eventually revealed that those who are claimed by the Beast may lose their physical forms, and the Pumpkin People of Pottsfield are the result of that; they are slowly being eaten away by the Beast’s power, but they still try to go on living their usual lives within their pumpkinheaded shells. These are some of the friendliest and yet most deeply unsettling characters on this countdown at the same time, and that is saying a lot on both counts, as we’ll see going forward.

7. Merv Pumpkinhead, from Sandman.

I should note that I’m specifically referring to the character from the Netflix TV series version of “Sandman,” as I am woefully unfamiliar with the comics, where Mervyn “Merv” Pumpkinhead I believe has a larger role. Even though he’s a relatively minor character in the Netflix series, in comparison, he still manages to make a big impression. Visually inspired by Jack Pumpkinhead from the Oz series (more on him later), Merv is a very different character in spirit: he is cynical, cantankerous, snarly, tough, and eternally sarcastic. Merv is the janitor of the the Dreaming, and essentially fills the role of local handyman: he’ll mop the floors and fix cracks in the windows and all sorts of other little jobs here and there, but he also knows where all the demolition equipment and weapons are kept, and he has no problem using them. He also has no problem voicing his doubts and sniping back at his employers - Morpheus and Lucienne - if he disagrees with them, speaking bluntly and plainly about any issues he has. It’s no surprise that, towards the end of the show, he’s one of the few characters willing to stand up to The Furies with intended-to-be-lethal force: Mervyn doesn’t take bull from anybody, least of all those who may mean the Dreaming harm. Part of the joy of the character, of course, comes from the novelty of his voice actor: Merv is voiced in the Netflix show by Mark Hamill, and I think the reason why that’s awesome hardly needs further explanation. The only reason he isn’t higher is simply because I wish there had been more of him.

6. Jack O’Lantern, from Billy & Mandy’s Jacked-Up Halloween.

Voiced by the inimitable Wayne Knight in this Halloween special for the classic creepy-and-crazy Cartoon Network series, Jack O’Lantern is a character very, VERY loosely inspired by the folkloric figure of the same name. For those who don’t know, the legend of Jack O’Lantern - in brief - tells of a trickster by the name of Jack who played pranks on the Devil himself, only for his scheming ways to lead to his own downfall. In the “Billy and Mandy” Universe, it isn’t the Devil, but instead the Grim Reaper who Jack fools. It’s revealed that Jack stole Grim’s scythe, but agreed to return it to the Reaper in exchange for immortality. Grim, however, had the last laugh: he agreed to these terms, but as soon as Jack held up his side of the bargain, Grim lopped off his head with his scythe. Jack - unable to die, obviously - replaced his stolen skull with a carved pumpkin. In “Jacked-Up Halloween,” he plans to take revenge by pilfering the Reaper’s scythe once more, and - using its power - summon a horde of demonic pumpkin monsters to create a Halloween that never ends. I absolutely LOVED Jack O’Lantern; he’s easily one of my favorite villains, if not my favorite villain, from Billy & Mandy; I’m a sucker for trickster characters, especially those who go off the deep end. A big part of the nostalgia isn’t just due to the episode, though, but also a game: the episode inspired a platforming web game called “Harum Scarum,” in which the player can control Billy and/or Mandy on a quest to defeat Jack’s pumpkin army and then face off against the pumpkinheaded prankster himself. I played that game a LOT of times as a kid, and I still have fond memories of it. For both the show and the game’s sake, I feel I have to give this Jack O’Lantern a decent place…but I think there are a few other characters I like more who take the top five.

5. Samhain, from The Real Ghostbusters.

One of the most memorable villains from the Ghostbusters animated series, “The Real Ghostbusters,” Samhain is the literal Spirit of Halloween…and that’s not necessarily a good thing. This frightful pumpkinheaded entity believes that ghosts and other such “creatures of the night” are superior to human beings, and wishes to - you guessed it - take over the world, and repopulate it with supernatural agents of all sorts. He is one of the most powerful beings the Ghostbusters ever faced, and commands legions of spooks and goblins, whom he refers to as if they were his children. While he genuinely seems to want to make the planet a better place for ghosts…well…the problem with that goal is that means anything LIVING will have to go, or at least suffer, in his mind. And he absolutely loathes ghosts who side WITH humanity, seeing them as traitors to their own kind…think of him as a sort of spookier version of Magneto: an extremist of the most ghastly variety. Even though he only showed up in a couple of episodes of the original show, the character is still considered one of the most well-known and popular members of the Ghostbusters Rogues Gallery, and has continued to appear in comics and other spin-off media since. It’s not hard to see why: not only are the Halloween-y origins always a fun start, but his grotesque appearance and extremely creepy voice make him easily one of the most nightmarish fiends the Ghostbusters ever faced (and that’s saying a lot).

4. Lord Pumpkin, from UltraForce.

Ever wondered what would happen if you slapped a Pumpkinhead on Professor Moriarty? No? Good, then you have some semblance of sanity left…but that IS essentially the kind of character Lord Pumpkin is. Lord Pumpkin, also referred to affectionately as “Pump,” is one of the primary villains of the Ultraverse - a now-mostly-defunct universe of superheroes originally created by Malibu comics, but now (if I’m not mistaken) currently owned by Marvel Entertainment. His origins are that he was created as a pumpkinheaded, scarecrow like “plaything” for a spoiled prince, and given life by a wizard. Unfortunately, the Prince - who was beyond just “spoiled,” the kid was a freaking psychopath - heinously abused his “playmate” in a variety of ways. Eventually, the magical pumpkinhead had enough, and rebelled against his creators, eventually overthrowing the kingdom. Mad with power, Lord Pumpkin eventually grew bored of terrorizing his home universe, and thus decided to travel to our own world, planning to find new ways to torment and eventually conquer humanity. Pumpkin is essentially a classic archetype of a criminal mastermind: he is eloquent, frequently polite, and highly theatrical - a fan of Shakespeare, among other things. Frequently, the pumpkinheaded fiend is assisted by his young henchman, Pistol: a sort of modern day Artful Dodger who dresses up and speaks in a style reminiscent of old-timey movie mobsters. (Pistol, in fact, seems to be the only person the evil Jack O’Lantern warlock actually cares about. I really love that.) Pump is a powerful sorcerer, granted many incredible abilities by the magical candle hidden inside his Jack O’Lantern head…but his great weakness is that while he has a lot of power, his body is highly fragile. He’s ultimately still just a scarecrow with a pumpkin for a head; if you can damage his body, you can defeat him…but this is often easier said than done. On top of that, as long as even one of the seeds from whatever gourd his head is made from survives the attack, Pump can always find a way to quite literally grow back and return to bedevil the world again. While the character has not been seen in a VERY long time - Marvel hasn’t really done much with the Ultraverse since it snagged it (although Pump DID have an encounter with Loki, of all characters, interestingly enough…Loki won) - I actually would love to see him make a comeback. While much of the Ultraverse isn’t anything to write home about (there’s a reason it never really caught on), he’s legitimately a REALLY fun and cool villain, one who I can easily see lined up among some of the great supervillains of history despite how obscure he is. The character also had several appearances in the equally obscure UltraForce cartoon show…and, once again, his appearances are really the only ones worth looking up. He’s not a character a lot of other folks would likely know about or place in their top five, but he definitely rates highly for me.

3. Jack Skellington, from The Nightmare Before Christmas.

I debated whether or not I should give our favorite King of Halloween such a high spot…but only briefly. Technically, Jack Skellington ISN’T a pumpkinhead…he’s a skeleton. Most of the time, he appears in that form. HOWEVER, not only are pumpkins just a big part of his character - he’s called the Pumpkin King, often seen around pumpkins, the door to the world he rules over is shaped like a pumpkin, etc. - but he IS shown to sometimes take on the form of a pumkinheaded scarecrow. In fact, that’s how we first meet him in the film: as we enter Halloween Town, we see a pumpkinheaded dummy on a sign post, which spins and points the way towards the graveyard…and then later, the Halloween Town citizens perform a celebratory ceremony. The scarecrow suddenly seems to come to life, sets itself ablaze, and performs a dance before leaping into a fountain in the town square…only to then reappear as Jack Skellington proper. This sequence is so memorable, that various spin-off materials of “Nightmare” make full use of this “Pumpkin King Form.” There have been toys of Jack featuring this form: for example, I used to have a plushy where you could put the pumpkin “mask” on with velcro, then remove it to reveal the real Jack underneath. Multiple video game appearances - from Oogie’s Revenge to freaking Fortnite, of all things - have also taken advantage of this second skin, either just for decoration or as a means of providing the player (via Jack) with some special new abilities. Bottom line, while it’s arguably cheating, I think the pumpkinhead motif with Jack is strong enough to still give him SOME credit…and hey, one person recently pointed out to me that even his actual skull looks more like a carved white pumpkin than a real human head, so…there’s that, too, I guess. Ha Ha.

2. The Headless Horseman of Sleepy Hollow.

If there is an “OG Pumpkinhead” character, it’s got to be the Headless Horseman from Washington Irving’s “The Legend of Sleepy Hollow.” Which is sort of funny because, technically, that’s not how things work out in the book. In the original book, when Ichabod meets the Horseman, he sees what he THINKS is the dark rider’s head nestled in the pommel of the spectre’s saddle. He never gets a good look at what it is. It’s not till later that it’s revealed what the Horseman threw at Ichabod during their great chase was apparently a carved pumpkin. This is all intended to add to the ambiguous nature of the story’s ending, as it’s left unclear whether the Horseman that Ichabod Crane met was a real ghost, or just Brom Bones - Crane’s rival - in disguise. However, the visual of the pumpkinhead in placement of a real one has become SO iconic, it’s now just accepted as part of the lore of the character in nearly every other interpretation. Most versions of the Horseman - in illustrations, animation, and so on - don’t make any secret of the fact his “head” is a Jack O’Lantern. Instead, it becomes part of the mystique: it’s the replacement the Horseman has till he can either retrieve his own long-lost cranium, or chop off another that will suit his purposes. Some versions of the Horseman go a step further, outright giving him a pumpkinhead in the traditional sense rather than just carrying one around (a-la Billy & Mandy, I suppose). Even in versions where the Headless Horseman never DIRECTLY features a pumpkinhead tend to have allusions to this visual: for example, in the FOX Sleepy Hollow series, the Horseman ghoulishly turns the heads of some of his victims into human Jack O’Lanterns, and is later tricked by Ichabod and his allies into chasing after Halloween decorations while searching for his actual skull. Probably the craziest use of the pumpkin was in the animated Halloween special “The Haunted Pumpkin of Sleepy Hollow,” where if the Horseman manages to retrieve his pumpkinhead and place it upon his shoulders before midnight, he will gain the power to - what else? - take over the world. (Because I guess even the Headless Horseman needs to show he can be a supervillain sometimes.) Again, it’s ironic that all this hullabaloo about the pumpkin started because of an element intended to be vague and curious in a story that wanted to have a mysterious ending: the detail of the “pumpkin head” was never meant to be so literally taken, I suspect…but it’s now a big part of the character and his appearances in all forms of art and media, so I think it ultimately does count. And given my love of the Sleepy Hollow story, it’s no surprise this character ranks so highly in the ranks.

1. Jack Pumpkinhead of Oz.

Jack is by no means the scariest of all the characters on this list. Literally everybody else on this countdown is a lot scarier. But alongside the Headless Horseman, I would argue he is the most classic example of a pumpkinhead character…heck, the name “Pumpkinhead” pretty much starts WITH him, if I’m not mistaken, and the visual of a living scarecrow with a Jack O’Lantern skull as a popular character design basically starts here, too, at least as far as I’m personally aware. (If anyone wishes to correct me, be my guest.) Jack first appeared in the second Oz book, “The Marvelous Land of Oz.” He was constructed by the novel’s main character - Tip, a young waif who is eventually revealed to be the long-lost Princess of Oz, named Ozma - as a way of pranking their caretaker, the wicked witch called Mombi. At first, Mombi WAS scared…then angry…then curious, and she decided to use the pumpkinheaded mannequin in a magical experiment, sprinkling a so-called Powder of Life upon the creature, thus giving him…well…life. Since then, Jack has been a major character in the Land of Oz, showing up frequently throughout the books, and even having a surprising number of appearances in other media. His most well-known appearance was the movie “Return to Oz” - which combined elements of a couple of the Oz books together, and went in a deliberately darker direction than the more popular 1939 “Wizard of Oz” film. In both this film, and his initial appearance in the books, Jack is depicted as a very sweet, frankly almost cuddly character. (And I say “almost” only because it’s a little hard to adequately “cuddle” a guy made of wooden sticks and, well…a big pumpkin.) He’s a gentle-hearted, often childlike soul who doesn’t have a lot of intelligence, but does have a big heart and, at times, shows a surprising amount of common sense. Throughout his later appearances in the books, this BASICALLY remains the same: the only thing that changes is Jack’s intellect. It’s revealed that Jack’s intelligence - at least after his first appearance - depends on the quality of the pumpkin he’s using, as he has to literally recycle his own head at regular intervals, since once the Jack O’Lantern he has spoils, it becomes MOST unsightly and useless to him. (If you’ve ever seen a rotting pumpkin, it’s not a pretty sight.) Some heads are smarter than others, but even if his brainpower is on the lower side of the scale, he is always consistently loyal and friendly. If you’re looking for a great pumpkinheaded character for the sake of spookiness alone, there are definitely creepier customers…but when it comes to the general, overall concept, I think this guy takes the cake for me, and earns Number One on my personal list of My Favorite Pumpkinheads. Case dismissed.

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