!!The Film

* AlternativeCharacterInterpretation: Is Stitches just another Mook, or is the greatest henchman in any medium? [[spoiler: Royal Pain is de-aged into an infant, and out of pure loyalty, takes her in and raises her as his own daughter. And once she's old enough for her powers to manifest, he willing resumes his old position as her henchman.]]
** Stitches' boss, [[spoiler: Gwen]], is a veritable fountain of alternate interpretations: [[spoiler: Does she have any memories of her time as Sue Tenney, or is she just going by what Stitches told her? Is she mentally 17 or 45? Does she pick on Layla just to be an AlphaBitch or because Layla reminds her of where she came from? Did she genuinely love Will, or was he just a valuable pawn who'd be Pacified at first opportunity? Is she the inevitable result of the FantasticCasteSystem, or is she [[DisproportionateRetribution totally out of line]]?]] You can find support in the film for all of these, and resolutions to none; perhaps the never-made sequels would have revealed some of them.
* AwesomeMusic: The opening scene is set to "Everybody Wants To Rule The World."
** Michael Giacchino's score, a good example being Royal Pain's Leitmotif.
* CrossesTheLineTwice: [[FridgeHorror "Remember when we used to]] [[CrowningMomentOfFunny use real citizens?"]]
* CultClassic: A surprisingly strong fanbase for a oneshot production unconnected to any of Disney's better-known properties.
* DieForOurShip: It happens, Will and Gwen being the most common victims. The weirdest are the Warren/Layla fics that bash ''both'', when you'd think they could just as easily be used as a convenient PairTheSpares.
* DracoInLeatherPants: Lash. He's quite possibly the least sympathetic character in the film, yet he has piles and piles of fanfics portraying him as some sort of sensual lover.
* EnsembleDarkhorse: "Freeze Girl" is an unnamed character with no lines, yet she has her own character filter at fanfiction.net and more stories there than Gwen does. It might help that she's {{Ship Tease}}d with Warren at the end. Lash also qualifies.
** Not to mention Ron Wilson, Bus Driver.
* EvilIsSexy: Royal Pain, obviously. An in-universe example happens when Coach Boomer is trying to convince Professor Medula to go on a double date. Boomer tells Medula that the girl he's setting him up with is his own date's EvilTwin. Medula is sold at that.
* FanPreferredCouple: A portion of the fandom think Layla and Warren looked better together.
** Or [[FoeYay Will and Warren]]...
* FunnyAneurysmMoment: One of the crises Steve and Josie apparently have to deal with is supervillain infiltration of the IRS. Given that that agency would become mired in scandal in TheNewTens, one wonders if they were onto something.
* HarsherInHindsight: In some of the promotional material, Warren was jokingly declared [[http://disney.wikia.com/wiki/File:Warren.jpg "Most Likely To Become A Villian""]] in the Sky High yearbook. Then in the actual movie, it's revealed that Warren desperately wants to be a hero and live down his father's reputation.
* LauncherOfAThousandShips: Layla. There's a reason both of the DieForOurShip examples above directly relate to her romantic prospects. You've got your fairly obvious Will/Layla and Warren/Layla of course, but if you do a bit of digging you can find [[FoeYay Gwen/Layla]] and even ''Lash''/Layla, both of which tend to be [[{{Lemon}} seriously steamy]].
* MagnificentBastard: Royal Pain/[[spoiler: Gwen Grayson]].
* MemeticBadass: Ron Wilson, Bus Driver. Among other things, he must ''always'' be referred to in that way.
* MisaimedFandom: Warren fangirls ''really'' like parroting the inspirational line he gives Layla at the Chinese restaurant, ignoring the quite blatant fact that this is a ''parody'' of such lines, as five seconds later it's revealed [[FunnyMoments he's reading it off a fortune cookie]].
* MoralEventHorizon:
** During "Save the Citizen", Speed comes dangerously close to ''killing Warren by suffocation''. Could be seen initially as an unforeseen side effect of his attempt at dousing Warren's fire, until it's revealed that [[spoiler:Speed and Lash were evil the whole time...meaning that he might indeed have been doing it on purpose. ''[[ForTheEvulz For fun]]''.]]
** Baron Battle likely crossed off screen, considering the fact that he was heinous enough to get hit with a jail sentence that spans over ''multiple lifetimes'' with no parole.
* {{Narm}}: The "Pacifier" thing that regresses anyone into a baby.
** When [[spoiler:the school is falling]], Layla responds by screaming...that [[spoiler:the school is falling]]. Thank you, Layla, I'm SURE Will and Warren would never have figured that out by themselves.
* NarmCharm: If the "Pacifier" is viewed as a spoof of ridiculous [[TheSilverAgeOfComicBooks Silver Age]] villain schemes. And it would work well, if followed through on.
* OneSceneWonder: Cloris Leachman as Nurse Spex.
* RetroactiveRecognition: Holy cow, is that [[Film/ScottPilgrimVersusTheWorld Ramona Flowers]]?
** Years later, Layla is still the "support" for [[Series/TheFlash2014 another superhero]].
** Gwen's father is Jim Rash, in very early role. He'd go on to a much larger one as Dean Pelton on ''Series/{{Community}}'' and even won an Oscar for writing ''Film/TheDescendants''.
* RonTheDeathEater: Will is rarely turned outright ''evil'' in Warren/Layla fics, but he's often portrayed as a dull or neglectful boyfriend, and such stories often begin with something to the effect of "[[{{Anticlimax}} Will and Layla dated for three weeks after the movie before Layla broke it off because he's boring]]." Will is usually thereafter DemotedToExtra or at most paired with a background character. Gwen is also sometimes portrayed as a [[RealWomenNeverWearDresses vapid, "girly" bimbo]] [[spoiler:and her Royal Pain persona cranked UpToEleven (even though in-film she was a silly Silver Age-esque villain who only wanted mass-deaging and corruption rather than mass-murder)]] to justify Will/Layla. Most of this is done to make [[LauncherOfAThousandShips Layla]] look better for whatever choice the author selects for her, if you can't tell.
** Steve is also a semi-common victim of this, with his canonical preoccupation with the family name twisted into outright obsession. If Will is gay, he usually gets the obligatory [[PoliticallyIncorrectVillain designated homophobe]] role, too; one memorable fic has him throw Will out of the house upon discovering he's dating Warren, and Will's new father figure subsequently becomes, of all characters, ''[[TheDreaded Baron]] [[BiggerBad Battle]]''. The story ends with Josie leaving him for [[HopelessSuitor Mr. Boy]].
* ShockingSwerve: A curious example. [[spoiler:Gwen's [[DerailingLoveInterests sudden complete personality transplant]] from cool-if-somewhat-possessive girlfriend to AlphaBitch]] had no buildup whatsoever, ''however'', when considered with the film as a whole, a lot of seemingly arbitrary scenes that appeared to have no point suddenly make a lot more sense (the malfunctioning light fixture at the dance, for instance, and also Speed randomly walking in on Will and Gwen as they're about to have a moment). Amusingly enough, a number of reviewers claimed to have called this twist from the beginning, using the logic that [[spoiler:senior girls never date freshman boys]].
* SpecialEffectFailure: During the cafeteria fight scene, you can see the plexiglass shields protecting Will from the flames as he crawls under the lunch table. To their credit, though, they did use real fire instead of CGI.
** Speaking of CGI, there is ''a lot'' of ConspicuousCGI in this film.
* StrawmanHasAPoint: [[spoiler: In a [[SelfFulfillingProphecy weird, cyclical sort of way]], Gwen basically ends up proving her own point abut the destructive nature of the hero-sidekick dichotomy right]]. Possibly [[IntendedAudienceReaction intentional]], given that the characters in-universe seem to realize this at the end.
* UncannyValley: Lash when he stretches. It just looks...''wrong''.
* TheUntwist: Was anyone really surprised when [[spoiler:Speed, Lash and Penny]] turned out to be evil?
* VanillaProtagonist: Will. He's a rather flat character who doesn't have to work at anything. This really stands out when he's around a heroic [[Franchise/{{Batman}} Poison Ivy]] and [[WesternAnimation/AvatarTheLastAirbender Prince Zuko]].
* VisualEffectsOfAwesome: While not all of the effects have aged well in some regards (ConspicuousCGI is all over the place), some manage to look pretty good, like the flying bus, Penny's splitting and Sky High itself.
* WhatAnIdiot: Who was the fool that thought an individual with the ability to [[spoiler: to bend [[{{Technopath}} technology and machinery]] to their will]] wasn't anything less than a powerful superhero in the making? Short sighted doesn't really cover it. This is FridgeBrilliance: If it was the 70s or so, technology might not have been to the point where it was as important/used the same way as it is today, and so the power wouldn't have been seen as being as good. Also, the hero/sidekick slotting is treated ''way'' too cavalierly. [[spoiler: Being a {{Technopath}} isn't very flashy, after all.]]
** Will has a pretty stupid moment when Gwen tells him that she's going to have to build a fog machine by herself and that she needs a bunch of committee members to help her. Kid, you ''saw'' her rebuild an entire ray gun ''just by waving her hand over it!'' If she's seriously complaining about having to build a fog machine like it's ''so'' hard, she's probably lying.
* XMeetsY: ''Comicbook/{{X-Men}}'' (specifically the Creator/GrantMorrison era, where a lot of mutant powers were... less than useful) meets ''Literature/HarryPotter''. It was probably not coincidental that the film came out at the height of both ''Harry Potter'''s popularity and the superhero movie boom, ignited by, you guessed it, ''Film/{{X-Men}}''.
* TheWoobie:
** Mr. Boy. Sidekicks get little respect as it is, but the Commander, who is shown to be very nostalgic, doesn't even remember working with him and never mentioned him once to Will. A deleted scene shows that he was casually left behind, still tied up after the Commander and Jetstream first defeated Royal Pain.
** While it doesn't even come close to justifying her behavior, there's no denying that [[spoiler:Sue[=/=]Gwen]] got screwed over. Her supposedly Sidekick-level power was actually awesome, she was just literally [[BornInTheWrongCentury Born In The Wrong Decade]] for it to be effective. That said, [[spoiler: when she was effectively "reborn" in the modern day]], she had the option of using her power to be a great hero, but chose to be a villain instead, so her fate at the end of the film is no one's fault but her own.

!!The Manga
* AwesomeArt: There's a lot of it.
* TearJerker: Ayame singing at the end...
** [[spoiler: The two little girls killed in a car crash deliver a last goodbye to their parents and schoolmates - on Christmas, no less.]]