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Gourd, Better, Best: Ranking 13 Pumpkin-Headed Characters
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Gourd, Better, Best: Ranking 13 Pumpkin-Headed Characters
From the deadly and demonic to the whimsical and wonderful — also, one of these guys raps for some reason?!
By Lorna Wallace
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Published on October 22, 2025
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I absolutely love characters who have pumpkins for heads—not only are the gourds so perfectly head-shaped, but they also feel so very Halloween-y! Given that we’re in the spookiest month of the year, I thought now would be the ideal time to gather together all of the onscreen pumpkin-headed characters that I’m aware of and rank them to see who’s the greatest pumpkinhead of all!
Before I start, here are a few rules and notes:
I’m only considering characters from films and TV shows—pumpkinheads from books, comics, and video games are excluded.
I unfortunately won’t be including R.L. Stine’s Pumpkinhead (2025), simply because it wasn’t available to watch at the time of writing.
While I might mention what I think of the film or show as a whole, the positions on this ranking are based entirely on the quality of the individual pumpkinheads themselves.
Also, a quick content warning: If you haven’t seen the movies and shows discussed below, please be aware that some of the clips and trailers contain disturbing and violent imagery, so use your discretion if you want to avoid horror and gore. With that said, onto the rankings—let’s find out who’s carved out the top spot as King of the Patch!
13. Pumpkinhead from Pumpkinhead (1988)
You might be surprised to find a character literally named Pumpkinhead at the bottom of the ranking, but despite what the moniker might lead you to believe, Pumpkinhead is unfortunately the least pumpkin-headed character of the bunch.
Pumpkinhead sees grieving father Ed Harley (Lance Henriksen) seeking out the help of a witch in an attempt to avenge his son’s accidental death at the hands of a group of rowdy teens. Ed digs up a desiccated corpse from the pumpkin patch graveyard and the witch performs some magic to bring the vengeful Pumpkinhead to life.
Although regarded as something of a cult classic, the creature design is actually the only thing I really like about this film. But for the purposes of this ranking, that design is a let-down on the pumpkin front: I won’t deny that Pumpkinhead has a very large round head, but it’s only vaguely pumpkin-shaped and doesn’t really live up to the name.
12. Sawtooth Jack from Dark Harvest (2023)
Dark Harvest is an adaptation of Norman Partridge’s 2006 book of the same name. Each October 31st, a small rural farming town sends out its teenage boys to hunt down a pumpkin-headed and candy-filled monster known as Sawtooth Jack (a.k.a. the October Boy). The stakes in this hunt are high: if the boys fail and Sawtooth survives the night, then the town’s crops—the lifeblood of the community—will die. (There’s actually a little more to it than that, but those are the broad strokes.)
The trailer doesn’t provide a great look at Sawtooth Jack (though if you don’t care about spoilers for the very end of the film then you can check him out in this clip), but while his head is pumpkin-shaped, it’s distinctly lacking the iconic orange color. I might be biased because I read the novel first, but for me the film version of Sawtooth doesn’t live up to the description of him in the book.
11. The Headless Horseman from The Adventures of Ichabod and Mr. Toad (1949)
The Legend of Sleepy Hollow segment of this beautifully animated Disney classic ends with a scene that brilliantly mixes horror with humor (and both are of the child-friendly variety). When Ichabod first spots the Headless Horseman, the supernatural rider is holding a flaming jack-o’-lantern. The carved pumpkin never actually sits atop his neck in this rendition of the story, which makes me question whether he counts as a pumpkin-headed character, but I’m going to allow it.
The Jack-o’-lantern also isn’t all that present throughout the subsequent chase (which begs the question: where exactly is the horseman putting the pumpkin while using both hands to hold onto the reins?), but it’s used to great effect right at the very end [spoiler warning]. Just when Ichabod thinks he’s reached safety, the horseman lobs the flaming gourd directly at the camera. The next morning, all that’s found are the crushed pumpkin and Ichabod’s hat. It’s a surprisingly chilling ending for a kid’s movie.
While I love the animation and the use of the jack-‘o-lantern as a weapon, I do feel like I’m stretching the limits of what could be considered a pumpkin-headed character, hence the fairly low ranking.
10. Samhain from The Real Ghostbusters (1986)
It’s Halloween and the animated versions of the Ghostbusters are already feeling overworked by the abundance of ghosts causing mischief on the spooky holiday when they encounter a particularly powerful entity: Samhain, the spirit of Halloween. Not only does Samhain plan to make every day Halloween, he can also seemingly control almost all other ghosts (Slimer is able to resist). I find Samhain’s character design to be deeply unsettling—largely due to the fact that he has human gums and teeth in the mouth of his pumpkin head. And while I appreciate his motivation, it pains me that both he and the Ghostbusters mispronounce “Samhain” throughout the episode (the name of the ancient Celtic festival is actually pronounced “sah-win”).
9. The Killer Pumpkin from Carved (2024)
Carved didn’t really work for me as a movie overall—the comedy didn’t land and the characters were bland at best and irritating at worst—but I can’t deny that the killer pumpkin itself looks fantastic. This sentient squash is picked to be part of a pumpkin carving contest and on witnessing its orange brethren being hacked and stabbed, it decides to take revenge against every human who participated in the pumpkin murderfest.
Carved’s killer pumpkin largely appeals to me because it’s brought to life via practical effects—it’s essentially a big puppet. And although this pumpkin isn’t attached to a body (which is my preference for pumpkin characters), it more than makes up for that by being a bumpy, lumpy, and warty titan of its kind, sporting an impressively gnarly face. It doesn’t let its lack of legs slow it down either, using its vines to move around at some pretty fast speeds.
8. The Grand Pumpkin from The Simpsons “Treehouse of Horror XIX” (2008)
“It’s the Grand Pumpkin, Milhouse”—an obvious riff on It’s the Great Pumpkin, Charlie Brown (1966)—is the final tale of terror in this Halloween episode of The Simpsons. While Linus’ dreams of the Great Pumpkin never come to life, Milhouse’s do—expect it all turns into a nightmare. After being fed pumpkin bread, witnessing jack-o’-lanterns being carved, and being offered pumpkin seeds (“you roast the unborn?!” he exclaims in horror), the Grand Pumpkin decides to devour the people of Springfield.
Although the Grand Pumpkin has the same MO as the pumpkin from Carved, he wins a higher spot on this list thanks to his hilarious dialogue and overall design. I love how oversized his head is—it looks downright precarious balanced atop his skinny stalk body (and having a body at all wins points with me!).
7. The Pumpkin Rapper from Mighty Morphin Power Rangers “Trick or Treat” (1994)
The Power Rangers have fought many, many weird monsters in their time, but the Pumpkin Rapper must be one of the strangest. He is, quite literally, a pumpkin person who communicates via rap. It’s ridiculous and his rhymes are terrible and I love it. Nothing about this character makes any sense. Why does he rap? No idea. Why is his jack-o’-lantern head on upside down? Don’t know. Why does he have electric powers? Again, I haven’t a clue. But this nonsensical silliness is what makes the Pumpkin Rapper such a fun character in my eyes—and clearly other people think so too, because he pops up a few more times in the Power Rangers franchise.
6. Jack O’ Lantern from The Cabin in the Woods (2012)
[Spoiler warning.] This is an admittedly high position for a character whose screen time essentially amounts to a couple of seconds in the background, but I think he’s earned it.
There’s a huge variety of monsters that could have been unleashed on the college kids staying in the titular cabin in the woods. We get a glimpse of this near the beginning of the film, with a betting board in the mysterious underground lab listing many different creatures, including Jack O’ Lantern (the security team bet on him). Out of all of the options, it’s the “Zombie Redneck Torture Family”—a.k.a the Buckner Family—that’s ultimately chosen (congrats to maintenance and Ronald the intern!)
We apparently get a peak of Jack at the end of scene where Dana (Kristen Connolly) and Marty (Fran Kranz) see the glass cubes that house the monsters, but I’m not sure where he is. Regardless, his shining moment comes when Dana triggers the system purge and all of the monsters are set free. Amidst the bloody chaos, a very short clip of Jack breathing fire is shown on a security camera. Given that jack-o’-lanterns are lit by candles, it just feels right that such a monster would breathe fire—plus, it looks cool, even in this tiny glimpse. If Jack had gotten more screen time, he’d likely be ranked even higher than this.
5. Sam from Trick ‘r Treat (2007)
All of the stories in anthology film Trick ‘r Treat are set on Halloween night and take place in the small fictional town of Warren Valley, Ohio. Just one character features in each spooky tale: Sam (Quinn Lord)—a small child wearing orange footie pajamas and a burlap sack over his suspiciously spherical head.
[Spoiler warning.] Sam doesn’t have a massive impact on any of the stories—instead featuring as a minor, mysterious figure—until the last section of the film. After witnessing the Halloween-hating Mr. Kreeg (Brian Cox) messing with trick-or-treaters, Sam goes on the attack. During their fight, the burlap sack is torn from Sam’s head, revealing a massive skull-pumpkin hybrid.
I’m not exactly sure what Sam is supposed to be—a physical manifestation of the spirit of Halloween, a Halloween demon, or something else—but I certainly appreciate both his look and his commitment to protecting the rights of trick-or-treaters. And while his name is presumably derived from Samhain, I’m giving him a pass on pronunciation since it’s shortened and the correction pronunciation is used elsewhere in the film.
4. The Jack-O’-Lantern Mask from Halloween III: Season of the Witch (1982)
Halloween III isn’t a particularly beloved film, partly because it’s a major outlier in the Halloween franchise, being the only film that doesn’t star slasher Michael Myers. But while Michael and his iconic Captain Kirk mask (yes, really!) are absent, masks of a different kind take a starring role in the film. Dan O’Herlihy plays the evil owner of Silver Shamrock Novelties who plans to sacrifice millions of children on Halloween night via microchipped masks designed to activate when an irritating commercial jingle plays.
Sure, the film is pretty bizarre (did I mention that the microchips have tiny bits of Stonehenge in them and that’s how they have the power to kill?) and its distinct lack of Michael Myers means that it doesn’t really feel like a Halloween film, but I’ve still got a soft spot for it. The scene where one of the jack-o’-lantern masks is activated is a particular highlight: Death by pumpkin mask is a nasty way to go, and the practical effects really sell this scene. The mask essentially rots on the young boy’s head, and once it’s done killing him, bugs and snakes—which are clearly real—start spilling out and writhing across the floor…
3. Enoch and the Pumpkin People from Over the Garden Wall (2014)
In the second episode of Over the Garden Wall, brothers Wirt (Elijah Wood) and Greg (Collin Dean) stumble across the town of Pottsfield, where all of the residents appear to be made of pumpkins. The brothers reassure themselves that they’re just wearing pumpkin costumes, but there’s an underlying feeling of something being not quite right as the townsfolk celebrate their harvest festival.
I love the variety of pumpkin people that we get to see, with each resident looking a little different. And then there’s Enoch (Chris Isaak)—the gigantic leader of the town, whose deep voice feels soothing and menacing at the same time. Every element of this episode—and much of the show, honestly, including the gorgeous animation—manages to feel cozy and comforting and eerie and unsettling. This feeling persists to the very end of the episode—[another quick spoiler warning]—with the revelation that the pumpkin people are actually resurrected skeletons. It feels creepily cult-like, but not entirely sinister—after all, they aren’t forcibly recruiting members before their time. As Enoch remarks to Wirt and Greg as they head off on their journey, “you’ll join us someday…”
2. Jack Pumpkinhead from Return to Oz (1985)
For me, Jack Pumpkinhead is the quintessential pumpkin-headed person. Although his carved facial features don’t move when he speaks, I think that lack of movement is more than balanced out by the fact that he’s brought to life entirely through practical effects. Plus, he still has plenty of personality thanks to Brian Henson’s excellent voice acting and head puppeteering and Stewart Larang’s fittingly stilted body movements (Jack’s limbs are made of branches, after all).
Given that Jack hasn’t experienced much of the world, he’s adorably innocent and naïve, and despite his poor treatment at the hands of Princess Mombi, he’s still a good-nature gentleman. Jack feels like a whimsical comfort in an otherwise traumatic film. I’ve not actually seen Return to Oz since I was a kid but I’m betting that the scariness holds up—there’s just no way that Princess Mombi’s many heads and the Wheelers aren’t still terrifying.
1. Jack Skellington from The Nightmare Before Christmas (1993)
Jack Skellington (Chris Sarandon provided his speaking voice, while Danny Elfman provided his singing voice) may not wear a pumpkin head for long in the stop-motion classic The Nightmare Before Christmas, but the scene certainly packs a punch.
Our introduction to Halloween Town comes via “This Is Halloween”—a song that has become a spooky season staple. The first glimpse of the town is of a scarecrow with a lit jack-o’-lantern for a head emerging out of the darkness, followed by a quick tour of the town’s ghoulish (but friendly!) residents. Building up to the song’s big climax, the scarecrow is pulled into the town center astride a straw horse. The figure then dramatically sets himself alight before twirling around and diving into a fountain as the chanting reaches a fever pitch. Jack Skellington then emerges from the water wearing his signature pin-stripe suit and bat bow tie.
It’s quite an introduction, and while Jack never dons a pumpkin head again, the performance definitely makes him worthy of both his title as Pumpkin King and the number one spot on this list. You don’t get any closer to channelling the essence of the holiday than a skeleton dressed up as a flaming pumpkin-headed scarecrow while ghosts and ghouls chant along ecstatically to his iconic Halloween theme song.
This list is entirely subjective, of course, so if you feel I’ve overlooked your favorite pumpkin person—or missed them entirely—feel free to let me know in the comments, and happy Halloween![end-mark]
The post Gourd, Better, Best: Ranking 13 Pumpkin-Headed Characters appeared first on Reactor.