Illustration by Nick Wanserski

You may remember moments like these from your own childhood, or you may have already inadvertently passed some on to the next generation. You settle in on a rainy Saturday for an afternoon of classic, conceivably benign children’s entertainment. Suddenly you are struck by an unexpected moment that startles you so much, you know you’ll be fishing that nightmare fodder out of your psyche for years to come: winged monkeys, Wonka tunnels, terrifying transformations that turn boys into donkeys and Muppets and Smurfs into zombies. In honor of Halloween, we’ve plumbed the depths of our relative subconsciouses for a vast array of these moments, and discovered why the Brave Little Toaster had to be quite so brave. And if you’re really embracing the scary season, check out the supercut at the bottom of page. Who needs Halloween horror movies when Large Marge is around?

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1. Pee-Wee’s Big Adventure: Large Marge (1985)

Pee-Wee’s Big Adventure turns 30 this year, and even three decades later, Tim Burton’s first full-length movie is an imaginative, delightful romp, transporting the viewer to a world of magical bicycles and breakfast machines. Pee-Wee’s journey to find his stolen bicycle remains entertaining throughout, despite a few dark turns. Sure there’s Andy, Simone’s homicidal ex-boyfriend, some scary surgery-performing clowns, and a menacing motorcycle gang won over with an inspired version of “Tequila.” But for absolute shock value, nothing tops Pee-Wee’s lonely trek as he gets picked up by ghost truck driver Large Marge. The timbre of the movie shifts rapidly, as eerie organ music backgrounds a foggy highway, and Marge describes the mangled bodies in the worst wreckage she’s ever seen. And just when the viewer may be wondering how horrible this is actually going to get: Her face explodes in a moment that’s less a departure than a “what in the hell was that?” Burton would also use this random, out-of-nowhere effect in his follow-up movie, although there he kindly only shows Beetlejuice’s exploding face from behind. But anyone watching Pee-Wee for the first time, lulled into a false state of childlike complacency, was likely to bolt right out of their seats. Try as they might, they may never be able to scrub the image of Large Marge from their brains. [Gwen Ihnat]

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2. The Muppet Show: “You Do Something To Me” (1976)

The Muppets’ premier prime-time series had a knack for changing tones on a dime, best exemplified by the fact that all of its characters, no matter how prominent, were at constant risk of being blown up or eaten. This gives the show a marvelously chaotic sense of comedic tension, one that produced bizarre and occasionally startling moments like Kermit The Frog growing vampire fangs (and going after Vincent Price’s neck) or Tony Randall turning Scooter into a series of increasingly gruesome ghouls (and the most gruesome of all, The Great Gonzo). Such sudden and shocking transformations are at the center of “You Do Something To Me”—from the first­-season episode guest-­starring British polymath Peter Ustinov—which begins on a particularly unnerving note, as a sinister-­looking sorcerer pops into frame and skulks toward the pink puffball of a Muppet seated stage left. The canned laughter feels incongruous, but not as much as the sound effect that follows it: The booming combination of a laser blast and a detonation that precedes the sorcerer’s wicked tricks. As the song wears on, it’s not so much the various forms the puffball takes—a cat, a snake, a bearded­-and-horned devil—that disturb, but rather the sense that we’re witnessing some sort of Jim Henson-­endorsed torture, a sense reinforced by the character’s whimpering voice and upturned mouth. Ultimately, she gets her revenge, but it requires one last hit of that ear-shattering voodoo that “You Do Something To Me” does so well—and the most upsetting puppet design in a segment full of upsetting puppet design. [Erik Adams]

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3. Willy Wonka & the Chocolate Factory: The tunnel (1971)

While Willy Wonka & The Chocolate Factory isn’t the most benign children’s movie—Roald Dahl wrote the screenplay, retaining the dark “children learning their lessons” themes from his book—there is one scene that goes from unnerving to terrifying. As the prize-winning children and their parents travel from the edible candy room to their next destination via boat, Willa Wonka (Gene Wilder) steers them into a dark tunnel. The horrible children and their worse parents start freaking out—except Grandpa Joe and Charlie, of course—but with good reason: The boat picks up speed, Wonka sings a creepy song under his breath, and images flash on the walls. A bird meeting its death and bugs on a person’s face sickens the passengers, and the mysterious Slugsworth’s sudden image unnerves Charlie. Wonka’s song gets louder and scarier, with Wilder descending into his signature shouting madness. In a movie that’s already got plenty of dark moments happening against pastel-colored candy wonders, this scene is an early hint at the cavities hiding under all that candy. [Caitlin PenzeyMoog]­

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4. Toy Story: Sid’s toys (1995)

Pixar’s always been good at keeping their films out of the uncanny valley, that unsettling bit of theoretical geography where representations of objects look just close enough to what they’re supposed to be to be truly terrifying in their wrongness. But when the studio’s animators dive into the valley, as they do in this sequence from their first blockbuster film, they don’t bother to mess around. Trapped in the room of serial toy torturer Sid, astronaut Buzz and cowboy Woody cautiously creep around, jumping at shadows and falling objects in a way that feels comical and cartoonish… at first. But then Woody’s flashlight catches sight of something under Sid’s bed, and Toy Story, briefly, but swiftly, descends into horror. The reveal of the mangled creature lurking under there—known as Babyface, officially—ratchets up the terror in perfect little increments of increasingly awful wrongness. First, it appears in profile, with the spiky remnants of torn-out hair suggesting some ugly incident of past violence. Then its spider-like body clatters into view, dredging up arachnophobic memories on metal Erector Set legs. Finally, there’s the reveal of its full face, the empty eye contrasting upsettingly against its permanently smiling mouth. And as it rises up menacingly, the other victims of Sid’s sick experiments begin to creep out of the dark… [William Hughes]

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5. The Brave Little Toaster: Firefighter clown dream (1987)

The Brave Little Toaster is a weird, scrappy film in which five anthropomorphic appliances go on a cross-country road trip to find their master owner. It’s an odd premise to be sure, but it is a fun little adventure with a minimal score and some experimental, great songs. It also has a some genuinely creepy moments, like a scene of an air conditioner losing his mind, scores of objects plotting to tear apart the gang, and final scene in a junkyard that’ll give anyone goosebumps. But the most disturbing scene occurs when Toaster has a nightmare where he malfunctions while making toast for his master, causing a fire that has to be taken out by a firefighter–who is also a terrifying-looking clown. It’s followed up by the toaster’s worse fates–a wave of forks, falling into a bathtub while still plugged in–but nothing will make your spine crawl more than the image of a clown saying “Run” between gritted teeth. [Kevin Johnson]

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6. Who Framed Roger Rabbit: Judge Doom is a toon (1988)

Moviegoers reveled in the sheer innovation of Who Framed Roger Rabbit, as Robert Zemeckis somehow seamlessly blended the world of animation and live action in Toontown. Daffy and Donald Duck together! Cameo appearances by cartoon classics like Betty Boop and Dumbo! Yet there were signs that the movie was aimed a little above the kid audience level: Jessica Rabbit’s figure, for one. But nothing prepared young moviegoers for the creepy moment where Judge Doom survives being run over by a steam-roller, because he is in fact a toon himself. It’s hard to say what’s more terrifying: His hopping around in 2-D form or his ability to fly through the air with his horrific, googly eyes shaped like daggers. [Gwen Ihnat]

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7. A Goofy Movie: Hot tub scene (1995)

A Goofy Movie had a bit of a popularity resurgence when it celebrated its 20th anniversary earlier this year. It’s not perfect by any means, but it is enjoyable. It’s the story of Goofy and Max attempting to bond while on a road trip, and while it functions within the parameters of your typical ’90s Disney film—slapstick humor, plenty of songs—it deals with some pretty heady themes, like parental fears, patriarchal respect and neglect, and the impact of one’s legacy on one’s children. Nothing represents those ideas more than the hot tub scene, in which Goofy and Pete have a darkly intense argument about how to raise their respective sons. A far cry from the sillier moments that come before and after it, the hot tub scene’s shift in colors and tones comes off just like a horror film, reaching for some uncomfortable truths and complexities in how parents, particularly fathers, rear their children, particularly boys. [Kevin Johnson]

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8. The Smurfs: The Purple Smurfs (1981)

This is the “zombie episode,” where Lazy Smurf is bitten by a purple fly, which turns him into a nasty, purple monster. He starts barking out “Gnap! Gnap!” and bites the next smurf he meets. That Smurf turns purple, starts shouting “Gnap!” and the affliction rapidly spreads until the whole village is teeming with tiny purple monsters. Papa Smurf frantically tries to find a cure, but the Smurfs helping him get bitten one by one. He eventually does find a cure, but Smurfs are being bitten faster than he can cure them. Papa finds himself surrounded by a hundred snapping, growling, purple monsters, and he runs to his laboratory for another dose of the cure, but it’s too late—they get him too. The show lets you absorb that hopelessness for a minute before a deus ex machina saves the day: The purple Smurfs accidentally set fire to the lab, and the cure-infused smoke turns the whole village blue in a matter of moments. That kind of pat ending was typical of the show, but the overall tone of “The Purple Smurfs” is far closer to Night Of The Living Dead than the show’s usual lighthearted idiocy. [Mike Vago]

9. Dumbo: Pink elephants on parade (1941)

For most of its short running time, Dumbo is a straightforward parable. Dumbo, a boy elephant with extra large ears, is mocked for his appearance. He befriends a mouse named Timothy, (temporarily) loses his mother, but ultimately learns that his ears, which, when properly controlled, allow him to fly, are his greatest strength. It’s a sweet, uplifting story, albeit one that isn’t afraid to get emotionally brutal when necessary. But nothing in the first 45 minutes will prepare an audience for the bizarre fever dream that is “Pink Elephants On Parade.” After Dumbo and Timothy fall into a barrel of beer, they hallucinate almost four minutes of pure cartoon anarchy, a trippy fluorescent concoction of mildly sinister elements with no real narrative connection to anything before or after it. In context, it’s a disturbing cul-de-sac that leads nowhere and tells us nothing, yet still somehow feels at one with the rest of the film: just another reminder that the world is a strange, menacing place full of grinning lunatics, and even a magic feather might not be enough to save you. [Zack Handlen]

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10. The Last Unicorn: Mommy Fortuna’s death (1982)

We called out this scene earlier in the year, but it bears repeating, because frankly, we still haven’t fully gotten over it. The Last Unicorn, a whimsical fairy tale about love, loss, and dedication, rewards youthful attention by haunting dreams for years after viewing, thanks to an unwavering commitment to being creepy as hell. (Though as an adult, it’s mostly just weird.) Having been captured by Mommy Fortuna, a witch who runs a carnival that keeps magical creatures trapped in cages, the unicorn convinces young magician Schmendrick to release all of them. One of the beasts freed is the harpy, a violent and dangerous animal who immediately turns around to enact vengeance on Mommy Fortuna. Ripping her apart would be bad enough; what makes it truly unsettling is that Fortuna seems to embrace her fate, cackling and howling with madness gleaming in her eyes, as she opens her arms to welcome her own death. [Alex McCown]

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11. The Great Mouse Detective: Fidget’s surprise (1986)

Plenty of adult filmgoers can’t handle jump scares, so it’s a little cruel that Disney’s Great Mouse Detective inflicts them on small children. And it’s even crueler that most of them involve a creepy bat named Fidget, who’s already nightmare fodder in his own right. In the film’s scariest moment, Basil, Major Dawson, and their young client Olivia track Fidget to a toyshop he’s robbing. Fidget quickly ducks out of sight and a few moments later every wind-up toy in the shop starts playing at once—creating a melody that straddles the line between whimsical and eerie. Olivia becomes enchanted by a small baby bassinet and as she innocently pulls back the blanket to see the baby doll inside, Fidget lunges toward the camera with a yelp, teeth barred in a horrific grin. With that one terrifying jump scare, a whole generation of kids learned never to trust a quiet moment in an otherwise action-packed thriller. [Caroline Siede]

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12. The Neverending Story: The Nothing (1984)

Few children’s films hit harder, or live eternally in the consciousness, like 1984’s The Neverending Story. Based on the German novel Die Unendliche Geschichte (fitting that this phantasmagoric cautionary tale is German) the story is an allegory about the fragile beauty of children’s imaginations and the importance of reading. It’s hard to say if director Wolfgang Peterson viewed this bizarre material as a warning to a generation that would increasingly become slaves to video games, cable, and ultimately social media, but the message was certainly prescient. The antagonist is The Nothing, a swirling, chaotic void that destroys everything in its wake. The Nothing is laying waste to the fictional utopia Fantasia, and the only thing that can stop the destruction is a human child’s imagination. The film never panders to its demographic and there’s no comic relief or goofy characters to relieve the creeping existential dread. The Nothing is a force of nature and not “boo” scary, but it’s unstoppable, propelled by the death of childlike wonder and imagination. By embodying every child’s fears (death, the unknown, growing up, loss of innocence), The Nothing is essentially the boogeyman that is puberty. Thanks a lot, Germany. [Drew Fortune]

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13. Sesame Street: Count turns Ernie into a zombie (1976)

Bert and Ernie’s friendship is one of the most endearing parts of Sesame Street. The pair bickers, but it’s never anything serious; in fact, their interactions work so well because they’re generally always tucked away in their own little world, insulated from outside distractions or traumatic experiences. Perhaps that’s why a sleepover visit from Count Von Count threw such a wrench in the space-time continuum. When the number cruncher can’t sleep, it’s suggested he count sheep as a way to induce slumber. However, this idea backfires in a big way: Count stays up all night reciting numbers, and emerges refreshed the next morning, while Ernie turns into a tired zombie with bags under his eyes, stuck counting sheep in an unsettled monotone voice. It’s a jarring and frightening sight, because it’s such a far cry from the normally bubbly, cheerful Ernie who adores his Rubber Ducky. Thankfully, Zombie Ernie is only on screen for less than a minute in this transformed state, but it’s enough of an appearance to have a lasting negative impact on impressionable young viewers. [Annie Zaleski]

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15. The Wizard Of Oz: Winged monkeys (1939)

The movie canon of Frank L. Baum’s work is full of not-safe-for-children imagery (see below), but the winged monkeys just might top the list. In Baum’s book, the monkeys are enslaved by the Wicked Witch Of The West, but in the film version, their only motivation is to serve the green-skinned baddie. Dorothy and company make it out of the haunted forest, only to have the Wicked Witch’s minions swoop down and steal Dorothy and Toto and fly them away. What’s so scary about the winged monkeys are their size. They aren’t cute and tiny, but human-sized, lumbering after Dorothy with terrifying strength. Her buddies, who have protected her thus far, are no match for them, even the Tin Man with his ax, and especially not the Scarecrow. Dorothy has no shot against a bunch of monkeys who are strong enough to pick her up and fly her away. But it’s the sheer number of them that gives the winged monkeys their terrifying power. When they first start their attack, it’s not just a couple of monkeys, but hundreds of evil primates descending upon our heroes. Dorothy never had a chance. [Molly Eichel]

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15. Return To Oz: Evil Queen Mombi (1985)

Return To Oz places the audience in a fantastical utopia in ruins, with Oz transformed into a dystopian wasteland, ruled by homicidal Queen Mombi and a gang of freaky wheeler-type things. Return To Oz is wall-to-wall nightmare, a completely bummer trip devoid of candy-gloss Munchkinlands or uplifting travel songs. The grim death march begins with Dorothy (Fairuza Balk) narrowly escaping electroshock treatment before retreating to the ruins of Oz. The nightmare really ramps up when Dorothy encounters The Wheelers outside the ruins of Emerald City. Oddly reminiscent of Alex and his Droogs in A Clockwork Orange, these snarling, steam-punk baddies are evil incarnate, cackling and enjoying their amorality. The ultimate freakout is evil Queen Mombi, who is introduced playing a mandolin and oozing sweetly veiled menace. What Dorothy doesn’t know is that Mombi is a vicious psychopath with a powerful lust for decapitation. The madness reaches a fever pitch when Dorothy escapes the Queen, whose coterie of screaming human heads is a nightmare chorus of bloodlust and insanity. Yikes. [Drew Fortune]

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16. Sesame Street Presents Follow That Bird: Miss Finch (1985)

There’s certainly no shortage of creepy Muppets out there, but few people seem to remember Miss Finch, one of several antagonists from Sesame Street’s first feature film, Follow That Bird. As much as she means well (she’s a social worker who believes that Big Bird should live with his own kind), it’s hard to shake the fact that she’s an imposing full-bodied Muppet, one who has the agitated smoker’s voice of Oscar nominee Sally Kellerman, no less. And how about her eyelashes? Tar-black and slanted into a perpetual glare, those things were surely made from amputated tarantula legs. Miss Finch reaches maximum menace early on in the film when, after Big Bird has run away from his foster family, he catches Kermit The Frog’s late-night news interview with her on a TV in the window of a hardware store. She vows to find Big Bird wherever he is, and sure enough, she drives on-camera just moments after he drops his teddy bear in the mail and starts hightailing it back to Sesame Street. It’s as if Miss Finch has burst from the television screen Big was just watching, her red van the public-television equivalent to Michael Myers’ station wagon in Halloween—enormous, loud, and shark-like in its prowling. Hell, it even comes emblazoned with a state seal on the driver’s side. When Miss Finch leans her head out the window, looks around for Big Bird, then grunts in frustration and speeds off into the night when he’s not there, you can’t help but think the overgrown canary’s in deadly trouble, even though Finch’s intentions are (supposedly) altruistic. [Dan Caffrey]

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17. The Secret Of NIMH: Dragon the cat (1982)

What is it about Don Bluth and cats? An American Tail’s Tiger notwithstanding, Bluth’s animation studio was obsessed with depicting felines as sociopathic, slobbering monsters in the ’80s, the scariest portrayal being Dragon in 1982’s The Secret Of NIMH. When mousy protagonist Mrs. Brisby and the klutzy Jeremy the crow first see him, it’s from a distance. He frolics in some swamp grass, playfully leaping into the air at a couple of stray birds. By all accounts, he looks like a normal house cat. But the closer Dragon gets, the more terrifying he becomes, emerging from the orange light at the mouth of a log as if ascending from the bowels of hell. His ogre-like silhouette creeps into frame, followed by a truly grotesque face that’s made up of scars, teeth, and one milky blind eye. When he roars and starts pursuing Mrs. Frisby and Jeremy through the water, they may as well be running from a T. rex. Sure, the tabby probably looks normal to his human owners, but when you’re a tiny mouse or a slightly bigger crow, Dragon looks… well, like a dragon. [Dan Caffrey]

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18. The Dark Crystal: Skeksis (1982)

Although Jim Henson never intended for his work to be seen as mere “kids’ stuff,” by the early ’80s his workshop had acquired that reputation anyway. That status led many a clueless parent to rent The Dark Crystal for their Muppets-loving offspring, thinking that the fantasy adventure would have the same innocent appeal of Kermit, Miss Piggy, and the gang. Those illusions were shattered with the appearance of the Skeksis, an evil race of hateful monsters whose twisted alien faces resemble a hybrid of a vulture and a lizard and who are able to suck the souls, or “essence,” from living creatures and (gasp!) drink it. Their deformed features, genocidal agenda, and disgusting table manners are nightmarish enough, but throw an army of crystal bats and the Garthim, the Skeksis’ hermit-crab-like foot soldiers, into the mix, and you’ve got a generation of kids forever scarred by the knowledge that not all Muppets are nice. [Katie Rife]

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19. We’re Back!: The creepy crow mystery (1993)

For the most part, We’re Back!: A Dinosaur’s Story is a dopey, amiable animated kids’ film about force-evolved dinosaurs brought into the modern era to make children happy. The dinos are all bright colors, rounded edges, and celebrity voices; the singing T. rex voiced by John Goodman is introduced golfing and reminiscing about his life. There’s one scary scene where the underdeveloped villain de-evolves them from cuddly plush toys into roaring monsters, but for the most part, the film is about manic banter and mildly antic little-kid mayhem. But then the good guys win and fly away from the villain, and out of nowhere, a flock of evil-looking crows swoop in and… devour him? Evaporate him? Unmake him? It’s profoundly creepy, all the more so because it’s so unexpected and unexplained. Note to children watching: This is apparently just something crows do to people who are left alone for five minutes. Oh hey, do you sleep alone, in your own bedroom? And in the dark? Good luck with that. [Tasha Robinson]

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20. Pinocchio: Transformation of little boys into donkeys (1940)

Every parent worries that their child might someday fall in with a bad crowd, but few animated films underline just how bad a crowd can get as Disney’s 1940 adaptation of Carlo Collodi’s The Adventures Of Pinocchio. Not long after the Blue Fairy brings Geppetto’s marionette to life, Pinocchio is tricked into joining a puppet show run by rival puppeteer Stromboli and is led down a perilous path that ultimately takes him to Pleasure Island, a haven of debauchery where kids are drinking, gambling, smoking, and vandalizing. Sure, it sounds great, but there’s a catch: Eventually the kids are turned into donkeys to work in the salt mines. On the surface, it may seem a little silly, but it quickly becomes horrifying when Pinocchio’s new “friend,” Lampwick, begins to transform. First the donkey ears pop up, then the tail pops out of the seat of his pants, and then as he turns around to ask, “What’s he think I look like, a jackass?” he’s got the head of one. Realizing what’s happening to him, Lampwick begs for help, but it’s too late: The remainder of the transformation has already started to take place. While moviegoers only see his shadow as his body contorts, combine that with his horrific braying and you’ve still got the stuff of nightmares. [Will Harris]

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21. Thomas & Friends: Henry bricked in the tunnel (1984)

Stop-motion preschool favorite Thomas & Friends usually follows a simple formula. Thomas The Tank Engine, or one of his fellow locomotives, is prevented from doing his job efficiently by some emotion—jealousy, pride, ambition—which eventually causes a crash or other mishap. Stern but affectionate railroad boss Sir Topham Hatt firmly sets things right, and a valuable lesson is learned. Except in one first-season episode, things aren’t set right. Powerful but insecure Henry drives into a tunnel and refuses to leave, fearing that a pending rainstorm will damage his paint job (the engines on this show are overly concerned about their paint). Unable to reason with him or force him out of the tunnel, Hatt flies into a rage, bricking up Henry inside the tunnel like a demented Edgar Allan Poe villain. While the subsequent episode sees Henry pluck up his courage and ask to be released from his prison so he can go back to work, rain or shine, the first episode gives no hint that there’s a second part to the story, and merely ends with the haunting vision of Henry’s sad eyes peeking out from behind his brick prison, sentenced to eternal torment. [Mike Vago]

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