!!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.
* CrowningMomentOfAwesome: When the Commander gives the kids and Ron Wilson the hero award ''and actually refers to them as heroes.'' Made even more awesome with the WellDoneSonGuy moment right afterward with Mr. Boy: ''"Oh, and Jonathan - whatever you're teaching these kids, keep teaching them... it."''
* 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.
* DesignatedProtagonistSyndrome: 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]].
* 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. Lash also qualifies.
* FanPreferredCouple: A portion of the fandom think Layla and Warren looked better together.
** Or [[FoeYay Will and Warren]]...
* 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]].
* 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]].
* {{Narm}}: The "Pacifier" thing that regresses anyone into a baby.
** NarmCharm: If viewed as a spoof of ridiculous [[TheSilverAgeOfComicBooks Silver Age]] villain schemes. And it would well, if followed through on.
* OneSceneWonder: Cloris Leachman as Nurse Spex.
* RetroactiveRecognition: Holy cow, is that [[ScottPilgrimVersusTheWorld Ramona Flowers]]?
* 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]].
* 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.
* UnfortunateImplications: None of the female freshman we see are sorted into 'Hero' class. Admittedly Layla was only excluded because she refused to display her abilities out of principle.
** Also, if you don't have powers, you are automatically designated as a sidekick. Essentially it means in order to be accepted in your own community, you ''need'' powers.
** The solution to the [[HaveYouTriedNotBeingAMonster Have You Tried Not Being a Sidekick?]] problem is for Will to get powers. Don't read too closely into the potential analogies.
** [[spoiler:Will going out with Gwen, who turns out to be Royal Pain, who is quite a bit older than Will.]] Borders on paedophilia if you think about it. He even says after [[spoiler:Gwen reveals she's Royal Pain, "Oh my God, I made out with an old lady!"]]. Though it's strongly implied that the only reason she [[spoiler:knows she's technically in her forties is because Stitches told her, meaning she's both physically and mentally 17, even with a gap of only three years the relationship has a lot of somewhat disturbing "experienced person taking advantage of inexperienced person" undertones, which, given that she's a villain, was probably the point]].
* 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.]]
* XMeetsY: ''Comicbook/{{X-Men}}'' (specifically the 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.

!!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.]]