* SugarWiki/AwesomeArt: There's a very good reason those illustrations are the most memorable thing about the books: Stephen Gammell is a damn talented artist. If he wants to terrify the living crap out of you with his nightmarish twisted imagery, he will more than deliver. And while they certainly can't compare to Gammell's originals, Brett Helquist's illustrations do a good job of creating a gothic, Halloween-y atmosphere without completely traumatizing those of a weaker constitution.
* AlternativeCharacterInterpretation:
** After her AdaptationalVillainy in [[Film/ScaryStoriesToTellInTheDark2019 the movie]], some are starting to wonder if the Pale Woman from "The Dream" is as benevolent as the story made her out to be, and theorizing that maybe the thing she was trying to warn Lucy about in her dream was ''herself'', especially since the story ends with Lucy fleeing the house as soon as she sees her. It doesn't help that in some versions of the story, the Pale Woman is malevolent (in one version, she simply walks over to the protagonist chanting "Sweet dreams, sweet dreams, sweet dreams..." over and over, and the story [[NothingIsScarier ends there]]). Not to mention that Lucy wouldn't have changed course to go to the other town without receiving the warning in the dream. By having the dream, [[SelfFulfillingProphecy she wound up going right to the place she was warned against]].
** Is "Harold"'s illustration meant to show the titular scarecrow or [[spoiler:Alfred's dried skin stuffed with straw and mounted?]] The film interprets it as Harold, justifying his face as an old Halloween mask.
* BigLippedAlligatorMoment: The original illustration for "Oh Susannah!" is quite disconnected from the story. The story is supposed to be about a student's roommate being killed, while the illustration is . . . not. [[https://static.wikia.nocookie.net/scary-stories-to-tell-in-the-dark/images/2/24/Susannah.jpg/revision/latest?cb=20181022021857 It features a man riding through the night sky on a rocking chair, being pulled on a rope by some sort of dark, formless entity. Above him, the moon has a skull-like face with a single, reaching arm.]]
* CommonKnowledge: Its commonly stated that Harold the scarecrow's creators abuse him despite knowing he's a sapient being. In the actual story, Harold's creators are horrified when he grunts and keep their distance, but after a couple of days of Harold not making any noise, they decide Harold is a regular Scarecrow and it must've been a mouse or other animal that got inside Harold and made the noise. This is certainly TooDumbToLive, but not them knowing Harold is a living Scarecrow.
* CreepyAwesome: Aaron Kelly, Harold, and The Wolf Girl.
* EnsembleDarkhorse: Harold is easily one of the most recognizable monsters in the series. Having a name and backstory certainly helps.
** From the same story Thomas and Alfred have gotten popularity in big part from a certain YoutubePoop [[WebAnimation/TomServo3 Author]].
-->''Let's throw the cows in a fire!''
* FanNickname: "The face that shat a thousand pants" for the [[NightmareFace infamous]] "Haunted House" illustration.
* HilariousInHindsight: The [[http://horrorhomework.com/blog/wp-content/uploads/2013/12/scary-stories-to-tell-in-the-dark-no-thanks.jpg figure]] in the original illustration for "No, Thanks" bears a strong resemblance to [[Film/TheLastJedi Supreme Leader Snoke]].
** "The Bad News" wouldn't be [[VisualNovel/DanganronpaTriggerHappyHavoc the only work that has a baseball player named Leon,]] [[spoiler: [[VisualNovel/DanganronpaTriggerHappyHavoc who is also destined to die.]]]]
* HoYay:
** Thomas and Alfred, the two farmers from "Harold". More than a few fans have made ''Film/BrokebackMountain''-themed jokes about them.
** O'Leary and O'Riley, the two dead men from "Ba-Room"; exactly why and how the two men ended up dead in the same bed is never explained.
* JerkassWoobie: Harold the Scarecrow. Horrifying as his final deed is, you ''really'' saw it coming given how his creators treated him.
* MagnificentBastard: ''Scary Stories to Tell in the Dark 3: More Tales to Chill Your Bones''' "Maybe You Will Remember": The manager, front desk clerk, and in-house doctor at a posh Parisian hotel concoct a coldhearted yet brilliant coverup plot after a guest, June Gibbs, is diagnosed with bubonic plague. Knowing June's devoted daughter Rosemary is staying with her, the doctor sends her across town for some useless medicine, bribing the cab driver to take the longest route possible, then allows June to die. The manager then has the body moved, the room redecorated, and all employees involved told that they will be fired if they reveal the truth. When Rosemary returns, the clerk and manager insist they do not recognize her, and drive her to the brink of madness insisting that neither she nor her mother ever stayed there. The hotel staff even bribe the news and police to bury the matter, all in the name of preventing the panic that the return of the Black Death would bring.
* {{Narm}}: This line in the otherwise terrifying "Me Tie Dough-ty Walker!": "[[CaptainObvious His dog had never uttered a word before.]]"
* NarmCharm: George S. Irving (probably best known for playing Heat Miser in ''WesternAnimation/TheYearWithoutASantaClaus'') narrates all three of the audiobooks in the series. He gets so into the roles that even the sillier lines are delightful to hear.
* NauseaFuel: "The Hearse Song" describes in detail what will happen to your corpse when you die.
* NewerThanTheyThink: "The Wendigo" is not based on the original Native American folklore, but rather on an Creator/AlgernonBlackwood story first published in 1910.
* NightmareRetardant: The stories in the final chapter of each book are "supposed to make you laugh, not afraid".
** Also, in the video for "Clinkity-Clink" the wind noises. Wsstchwsstchwoo!
* OlderThanTheyThink:
** "The Bus Stop." According to Mr. Schwartz in the book's foreword, this story actually dates *to Roman times*. For the curious it's an adaptation of the Vanishing Hitchhiker legend.
** Apart from the main character being a Christian preacher, "The Haunted House" bears a strong resemblance to a story recounted by Pliny the Younger in the first century AD.
* OnlyTheCreatorDoesItRight: Stephen Gammell was the original illustrator for the books, and traumatized a generation with his haunting artwork. While his art was so controversial it eventually got replaced, fan opinion is that his artwork ''is'' the books, and the film adaptation enforces it by scrupulously re-creating his art with its creature designs.
* TheyChangedItNowItSucks: The books are being re-released to commemorate the 30th anniversary... with new illustrations. Many people who grew up being terrified by these books and their original, creepy illustrations are ''not'' happy. Thankfully, versions with the original, terrifying Gammel artwork were eventually rereleased and can be found along with the new, tamer Helquist editions.
%%* UglyCute: The illustration of the pale woman in "The Dream" .
%%** The titular character of "Sam's New Pet" is actually pretty adorable in its own way.
* UncertainAudience: Though the books are far from unpopular, much of the controversy lies within who the exact target demographic is supposed to be. The notorious illustrations are far too scary for children to handle, but the actual stories themselves are too cheesy for adults to find scary.
* WhatDoYouMeanItsForKids: The books are best known for traumatizing a generation of children with their less than child-friendly illustrations. Suffice to say, they spent the better part of two decades holding the top spot in ALA's list of most challenged books, and were only knocked out of the top ten after the publisher caved and re-released the books with less disturbing images.
* TheWoobie:
** Mina of "Just Delicious." A sweet, timid little lady who's married to a cruel, bullying jackass, and yet she still [[LoveMartyr tries to keep him happy]] with her [[SupremeChef excellent cooking]]. She accidentally eats his dinner one day, and is so afraid of what he'll do to her that she's willing to steal another liver --''[[IAmAHumanitarian from a mortuary]]''-- to cover her mistake. And then there's an [[https://www.youtube.com/watch?v=wsQXHQWAjeM animated adaptation,]] which ramps up poor Mina's woobie-ness by actually showing the DomesticAbuse the original story could only imply.
** The unnamed woman in "The Haunted House". Sure, her face is horrifying to look at, but one can't help but admit the way she died (her boyfriend ''violently strangled her to death'') is terrible.
** Alice in "The Dead Man's Hand." She's a nursing student at a school, and the other pupils come to resent her because she's "too perfect." Rather than being an obnoxious Mary Sue, though, Alice is a genuinely kind, friendly, cheerful woman who doesn't deliberately try to antagonize anyone. The other nursing students play a nasty prank by tying a corpse's hand to the light string in her closet--but the trick [[GoneHorriblyRight works too well]], and Alice goes insane, seemingly irreversibly. She was just trying to become a nurse and help others, and she ends up destroyed for it.
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