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  • Alternative Character Interpretation:
    • Is Stitches just another Mook, or is he the greatest henchman in any medium? Royal Pain is de-aged into an infant, and out of pure loyalty, he takes her in and raises her as his own daughter. And once she's old enough for her powers to manifest, he willingly resumes his old position as her henchman.
    • Stitches' boss, Gwen, is a veritable fountain of alternate interpretations: Does she have any memories of her time as Sue Tenney, or is she just going by what Stitches told her? The hint towards the former is that she references going through puberty twice and not being happy about it. However, her entire plan hinges on the heroes not retaining their former identities, which would imply the latter. It's also notable that she needs to steal back the original Pacifier, which may imply that she doesn't remember how she built it. Is she mentally 17 or 45? Does she pick on Layla just to be an Alpha Bitch or because Layla reminds her of where she came from—or also pragmatism as driving Layla away to be able to play into the illusion is the proper and logical next step? 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 Fantastic Caste System, or is she totally out of line? You can find support in the film for all of these, and resolutions to none.
      • That Gwen when approached and given an apology by Will about her "mother" Sue getting "killed" years ago results in the bombshell reveal that the two are one in the same, that Gwen was monologuing to Baby!Commander a moment ago about how "Sue" was a "visionary" whose "genius" was so viciously and humiliatingly dismissed speaks to the idea that she did have to relearn everything after being pacified. That said, her using the monologue to clearly self-aggrandize herself does speak to Sue having pulled through with her original personality throughout all those years instead—and that Baby!Commander recognizes Will also seems to count toward him still being exactly who he was in his own mind before being pacified as well (same as both Mr. Boy trying to communicate with Josie as a baby and Medulla clearly retaining his own personality as a baby too). That Gwen also doesn't like how Stitches calls her "Daddy's Little Girl" would also indicate that he's done it for years and she was never okay with it since it meant he for a time had more seniority than she did.
      • To a lesser extent, would her getting close to Will count as grooming? She is technically a teenager but is mentally an adult, about the same age that his parents are. What's more, Gwen was isolating him from his friends and gaslighting him, which are red flags for domestic abuse even without the supervillain agenda.
    • It's fairly easy to interpret the adults as the true antagonists of the story, though with one exception (two if Boomer is included) they aren't actively malevolent if not villains. The ultimate source of the conflict in the film is the Hero-Sidekick Fantastic Caste System they prop up, which places a tremendous amount of pressure on the teens from both their peers and superiors, to the point that Will is absolutely terrified of coming out as powerless due to what his dad's reaction might be. The classification is also exceedingly arbitrary, with Boomer seemingly having the first, last, and only say as to where an incoming freshman ends up - and Steve has reason to believe he deliberately washes some kids out due to bitterness over his own professional hero career failing. He declares Layla a sidekick for questioning this, even though it's later revealed she's seriously powerful. The caste system is also shown to lead to arrogant bullying on the part of the Heroes kids and resentment on the part of the sidekicks, both of which seem to be tolerated, and in some cases encouraged, by the school administration and both of which create supervillains. The one genuinely malicious adult is the aforementioned Stitches, who spirited the de-aged Royal Pain away and raised the girl to be a carbon-copy of the original - in other words, even the main villain of the film is the way she is because of an adult forcing her into a role.
    • When actual people were used in "Save the Citizen" tests, were they in real danger or were they just suspended over prop shredders and such?
  • Awesome Music: The film is filled with covers of 80's songs. Highlights are:
    • The opening scene is set to a cover of "Everybody Wants To Rule The World" that while nowhere as iconic as the original by Tears for Fears is quite nice on its own regards.
    • "Through Being Cool" by Devo is given a more energetic cover courtesy of They Might Be Giants.
    • Flashlight Brown's cover of The English Beat's "Save It For Later", which can be heard in the scene where Will and Layla are waiting for the bus for their first day of school as well as the end credits to the film, is an energetic tune that is simply all kinds of awesome.
    • The ending credits are played over Bowling for Soup's Pop Punk cover of "I Melt With You" by Modern English, and the song's as glorious as it sounds.
    • Michael Giacchino's score is no slouch either when it comes to the awesome, a good example being Royal Pain's Leitmotif. And the main theme.
  • Base-Breaking Character: Will. He's either a very realistic take on a teenage boy with all the flaws and quirks one would expect, or a selfish, neglectful person whose friends take him back way too easily.
  • Big-Lipped Alligator Moment: At one point during the party scene, Speed walks in on Will and Gwen as they're having a moment and makes a bizarre request for a bucket. We never find out what he needed one for, though it might have been an implication he was drunk and needed to puke or else something related to the supervillain scheme.
  • Cliché Storm: Both of the Superhero School and high school genres. How well it was played, however, is up to the viewer. Given it's more of a parody of the Super Hero genre, these were most likely intentional.
  • Crosses the Line Twice:
    • "Remember when we used to use real citizens?"
    • Coach Boomer tests Will's superpower potential by dropping a car on him. Keep in mind that this is before he knows for a fact that Will actually has Super-Strength.
    • Nurse Spex's incredibly blunt explanation for how getting powers works:
      Nurse Spex: Kids who get exposed to nuclear radiation or fall into vats of toxic waste usually have their powers manifest the next day. (Beat) Or they... Die.
    • Steve actually considering dropping Will in toxic waste in response to Josie's rhetorical aside wouldn't be funny, but her "No. Just… No" Reaction is.
  • Cult Classic: A surprisingly strong fanbase for a one-shot production unconnected to any of Disney's better-known properties—to the point that fan support for a sequel continued on over the years and director Mike Mitchell also saying he wanted to do it too.
  • Die for Our Ship: It happens, Will and Gwen being the most common victims depending on what ship is being supported. The weirdest are the Warren/Layla fics that bash both, when you'd think they could just as easily be used as a convenient Pair the Spares. And Gwen being subjected to this treatment is especially baffling given that the film pretty thoroughly sinks the Will/Gwen ship anyway since Gwen is actually the villain. And a de-aged adult.
  • Draco in Leather Pants: Lash. He's one of the least sympathetic characters in the film, yet he has piles and piles of fanfics portraying him as some sort of sensual lover.
  • Ensemble Dark Horse:
    • "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 Teased with Warren at the end.
    • Rubber Man bully Lash is pretty popular for his visually-impressive powers and a few humorous moments during scenes where he gets his comeuppance. 
    • Not to mention Ron Wilson, Bus Driver.
  • Fan-Preferred Couple: Both Warren/Layla and Warren/Will are more popular than the canon Layla/Will. The former because of their chemistry while pretending to date and the latter because of the Ho Yay between the two.
  • Foe Yay Shipping: Rather disturbingly, there is some between Steve Stronghold and Royal Pain ("My dear commander..."). And of course, Gwen and Will is revealed to be entirely this, if there was more to it than her using him to get the Pacifier.
  • Friendly Fandoms: There's a decent overlap between Sky High and My Hero Academia fandoms.
  • Harsher in Hindsight:
    • 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 The New '10s, one wonders if they were onto something.
    • In some of the promotional material, Warren was jokingly declared "Most Likely To Become A Villain"" 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.
    • The next time Kurt Russell played the father of the protagonist in a Disney-owned superhero movie, he was the one who turned out to be the secretly evil Big Bad.
    • The film has some noticeable similarities with My Hero Academia, even apart from being a school for superheroes, but the final arc of the latter shares a plot element with the climax of the former- the heroes trying to stop their school from falling out of the sky.
  • Hilarious in Hindsight:
  • Ho Yay:
    • Almost certainly unintentional, but consider that when Warren sarcastically asks if anyone else needs a date for homecoming, Ethan raises his hand, looking hopeful.
    • Will and Warren's growing respect for each other lends some.
  • Jerkass Woobie: While it doesn't even come close to justifying her behavior, there's no denying that Sue/Gwen got screwed over. Her supposedly Sidekick-level Technopath powers were actually awesome, she was just literally Born in the Wrong Decade for it to really be useful. That said, 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. Unless she did lose her memories and was raised to be evil and resentful by Stitches.
  • Launcher of a Thousand Ships: Layla. You've got your fairly obvious Will/Layla and Warren/Layla of course, but if you do a bit of digging you can find Gwen/Layla and even Lash/Layla, both of which tend to be seriously steamy.
  • LGBT Fanbase:
    • While no character in the film is explicitly stated to be gay, the film has a significant amount of gay fans on tumblr, who see the portrayal of anti-sidekick stigma as a good metaphor for homophobia.
    • Will's struggles of telling his parents that he has no superpowers while trying to come to terms with it is a strong analogy of a person wondering about his sexuality. Especially with the way his parents react when Will finally "comes out" to them. His dad is initially in denial, claiming that he will have superpowers (i.e., "be normal" by their metrics) and even considers "dropping him in a vat of toxic waste" to give him superpowers (i.e. "fix" what's "wrong" with him). His mom, meanwhile, while not thrilled that her son isn't who they wanted him to be, still insists that they can be "The Stronghold Three, the greatest family the world has ever known."
  • Magnificent Bitch: Sue Tenney, the original Royal Pain, is the mastermind of the film's conflict, puppeteering an Evil Plan spanning two decades. Once a bullied outcast at Sky High, Sue decided to get her revenge by creating the Pacifier, a laser cannon with the power to regress anyone it hits to a newborn baby. Taking the identity of Royal Pain, a presumably male villain, Sue aimed to regress all the students and teachers at the school into babies, whereupon she would raise them as her own generation of supervillains. Inadvertently turned into a baby herself in a fight with the Commander and Jetstream, Sue inspired such loyalty in her Sidekick Stitches that he was willing to raise her for seventeen years until she was old enough to begin the plan anew.
  • Memetic Badass: Ron Wilson, Bus Driver. Among other things, he must always be referred to in that way.
  • Memetic Mutation: The fact that there's not only a character literally named "Boomer," but the character in question is a resentful Jaded Washout who takes out his frustrations on his teenage students and is the main enforcer of the Fantastic Caste System, has seem a lot of traction in conjunction with the "OK, Boomer" meme of the late '10s.
  • Misaimed Fandom: 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 he's reading it off a fortune cookie.
  • Moral Event Horizon:
    • 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 Speed and Lash were evil the whole time... meaning that he might indeed have been doing it on purpose. 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.
    • The most heinous of all would be dropping the school through deactivating the anti-gravity device. Given the possible contents included in the school, Royal Pain and her minions are not only willing to pacify hundreds of people (including children) to raise as villains, but they're willing to destroy an entire neighborhood and potentially kill dozens of innocent people, just for revenge.
  • Narm: When the school is falling, Layla responds by screaming...that the school is falling. Yeah, we're sure Will and Warren would never have figured that out by themselves.
  • Narm Charm:
    • If the "Pacifier" is viewed as a spoof of ridiculous Silver Age villain schemes. And it would work well, if followed through on. Not to mention there is a problem if a flying superhero gets turned into a baby midflight; they can fall and badly hurt themselves, as seen with Jetstream when Mr. Boy dramatically catches her.
    • The constant use of overly dramatic music.
  • Nightmare Fuel:
    • "Save the Citizen" has a dummy being lowered into a wood-chipper Death Trap while saying "Save me" in a monotone Broken Record. Sure, it's fun to watch if you're a spectator but if you are a hero fighting the villain team and you fail to mount a rescue, you get a lovely shot of the dummy being turned to powder. Mr. Boy chuckles when recalling they used to use real citizens for this.
    • Speed nearly suffocates Warren during Save the Citizen, in what's supposed to be a friendly match. Even Will can't stand that; he takes care of Lash, goes to rescue Warren, and then rescues the dummy. Maybe you shouldn't try killing your classmate in front of his "nemesis".
    • The climax plays out like a mass shooting which makes it even worse:
      • Gwen reveals herself as Royal Pain, aka the Commander's archnemesis, and that she lured Commander and Jetstream into a trap at homecoming to use the Pacifier on then. Commander laughs because he says a gun can't kill him. Her plan wasn't to kill him; she shoots him, and he screams in agony before turning into a baby. She proceeds to do the same to Jetstream, and then Mr. Boy for risking his life to save Josie from a deadly fall. Royal Pain proceeds to mow down the adults as they try to coordinate to protect the students.
      • Crowd Panic ensues because even a bunch of teens with superpowers will act like scared kids when in an actual dire situation. They try to run for the exits, only to find that Gwen's lackeys have sealed the doors, with Penny blowing kisses at her classmates before walking away. Warren only gets the sidekicks out by torching the lid off an air vent and gesturing them to get inside.
      • Then there is Royal Pain's Evil Gloating to Will, who politely requests that she put his de-aged father down while expressing sympathy about their situation. The gleeful look in her eyes shows that she never truly cared about Will, that he was just a pawn in her scheme though now she has more incentive to get rid of him since he dumped her. Royal Pain complies with handing the Commander to Stitches, before continuing and explaining that she didn't have a mother, she was Royal Pain owing to the Pacifier turning her into a baby and Stitches raised her. Showing that Royal Pain is a Mood-Swinger, she yells at Stitches for calling her "Daddy's little girl".
  • One-Scene Wonder:
    • Cloris Leachman as Nurse Spex.
    • Tom Kenny and Jill Talley as the new homeowners who almost get crushed by the falling school.
  • One True Pairing: Every angle of the Gwen-Will-Layla-Warren love tetrahedron has its supporters and detractors, but most fans love Zach/Magenta.
  • One True Threesome: The third most popular relationship tag at Archive of Our Own, following the aforementioned Will/Warren and Warren/Layla, is... Will/Warren/Layla.
  • Retroactive Recognition:
  • Ron the Death Eater:
    • 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 "Will and Layla dated for three weeks after the movie before Layla broke it off because he's boring." Will is usually thereafter Demoted to Extra or at most paired with a background character. When he is made a villain, he's usually turned into a jerkass who let the fame he got from defeating Royal Pain go to his head and ditched his "sidekick" friends as soon as possible, a sharp contrast from his Accomplice by Inaction characterization when something similar happened in the movie proper.
    • Gwen is also sometimes portrayed as a vapid, "girly" bimbo and her Royal Pain persona cranked up to eleven (even though in-film she was a silly Silver Age-esque villain who only wanted mass-deaging and corruption rather than mass-murder, which would have only happened as a side-effect of the school drop rather than a goal in of itself) to justify Will/Layla. Most of this is done to make 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 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, Baron Battle. The story ends with Josie leaving him for Mr. Boy.
  • She Really Can Act: Mary Elizabeth Winstead is legitimately chilling in the scene when she conducts her Evil Gloating on a de-aged Commander. For most of the movie she's been the stereotypical Bitch in Sheep's Clothing, sweet-talking Will and putting down his friends, but more shallow than wicked. During this scene, she sports a menacing Slasher Smile while holding the baby, and hamming it up about her dreams to create a supervillain academy. She talks about how in the sidekick track, she was bullied by him and many others, so of course she had to become his archnemesis. Then Will shows up, and she turns up the Nightmare Fuel especially when she screams at Stitches. You can easily believe that she is an "old lady" in Will's words trapped in a teenage body
  • Special Effect Failure: 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.
  • Spiritual Successor:
    • It's probably the closest thing to a PS238 movie we'll ever see. Set in a Superhero School with the protagonist being the powerless son of Earth's greatest superheroes.
    • It's often considered a for intents and purposes remake of the Disney Channel movie, Up, Up and Away! which is about a family of superheroes where the youngest son has no powers.
  • Squick: Given that Gwen seems to have memories of being Sue Tenny — she references going through puberty twice— and she's mentally an adult while dating the TEENAGE Will, his response is Played for Laughs, but his situation can also be seen as Fridge Horror if she was actively trying to groom him; she was isolating him from his friends, gaslighting him and Layla, and using his attraction of her to distract him from her Evil Plan.
  • They Wasted a Perfectly Good Character:
    • Would have been nice to see Nurse Spex (X-Ray Vision), Medulla (Superhuman Intelligence, judging from the fact that he retains his intelligence even as a baby), and Coach Boomer (Sonic Scream) use their powers in a fight scene.
    • The cheerleader who shape-shifts into a beachball and is kicked off the stage by Boomer never becomes part of Will's gang (or even gets a name or any dialogue) when she could have been a Foil to more stereotypical cheerleader Penny.
    • Larry (who briefly gets along with Layla before the Power Placement scenes) and the Freeze Girl are both interesting but stunningly minor characters who could have served as more sympathetic representatives of the kids who were sorted as heroes instead of sidekicks. 
  • They Wasted a Perfectly Good Plot:
    • The extremely flawed Hero-Sidekick program causes the entire conflict of the film but is never resolved or even questioned. It gives terrible results in the form of heroes who become egocentric bullies who prey on the weak and sidekicks who become object of mockery and resent heroes. It is the opposite of what the school aims to achieve, and the root cause of almost all the movie's conflict, and yet the audience never learns whether or not it was abolished at the end.
    • Will's subplot in dealing with being a superhero without super powers would have been an interesting character arc for him. To be fair however it had been done five years earlier.
    • Layla is established as a Technical Pacifist; she says she'll only use her powers nonviolently and in a situation that demands it. The one time that she nearly breaks that rule is when Royal Pain seems to have killed Will, and she marches forward with murder in her eyes. Will shows up right then, revealing that he can fly, but it would have been interesting to see Layla's plant powers go toe-to-toe with Royal Pain.
    • The film could have further emphasized the Super Power Lottery putting some people in different social positions than in a normal high school (like geeky Larry being a hero and a cheerleader being a sidekick). Instead, the film mainly focuses on the sidekicks who already fit relatively uncool stereotypes.
  • Unintentionally Sympathetic: While most of the film hinges on the idea of Will coming to grips with his bad actions towards his friends and him abandoning them for the popular crowd, in reality even when he developed his powers, Will had no real desire to abandon his friends. Heck, in nearly every scene of him and Gwen, you see him make some attempt to still try to contact his friends in someway only to be pulled away by Gwen and her crew. The closest Will comes to becoming a jerkass is when he freaks out over Layla going to the dance with Warren (which in itself was understandable since up to that point Warren was an antisocial nutcase out to kill Will). But with that said, Will never really becomes the arrogant jerk the film tries to sell him as. An idiot who should have known that Gwen was obviously using him from the get-go? Sure. But a jerk? Eh, not really.
  • Unintentionally Unsympathetic: The sidekicks are quickly established as characters the audience is supposed to root for because the adults put them at the bottom of the Fantastic Caste System and their classmates bully them. But as soon as Will manifested powers they antagonize the villains as if he were their personal enforcer, even going so far as to challenge them to Save the Citizen, which Will clearly didn't want to do. And Will was supposed to be the jerk for ditching them?
  • The Un-Twist: Was anyone really surprised when Speed, Lash and Penny turned out to be evil? Will's reaction to learning of their betrayal is a blasé "Why am I not surprised?"
  • Vanilla Protagonist: Will. He's a rather flat character who doesn't have to work at anything. This really stands out when he's around the more interesting Layla and Warren.
  • Vindicated by History: The film received good reviews upon its release in 2005, but it was largely seen another Harry Potter imitator (only with superheroes!) trying to create stories in Hogwarts-esque Academies of Adventure, and only barely made it budget back at the box office. A decade later, the growing number of superhero-based works in film and television caused people to look back on the film as a more novel take on the genre and its conventions, especially for its surprisingly complex themes about social class and discrimination (the conflict between the heroes and sidekicks), betrayal (when the girl you fall in love with is really evil), and relationships between parents and their children. There's also the fact that, unlike the mainstream superhero movies that came out since, the film doesn't try to deconstruct or reinvent the genre, but plays its tropes relatively straight, while still telling a realistic story with believable characters, which is quite novel in comparison.
  • Visual Effects of Awesome: While not all of the effects have aged well in some regards, some manage to look pretty good, like the flying bus, Penny's splitting (help by Penny herself Making Use of the Twin) and Sky High itself.
  • Why Would Anyone Take Him Back?: A segment of the fanbase feels Will's friends, particularly Layla, accepted his apology for neglecting them too easily at the end.
  • The Woobie:
    • 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.
    • To an extent, Will. He lived most of his life fearing that he will never be able to measure up to his beloved parents, and by the time things turn around and he seems to be in his way to being a hero, not only does he nearly lose the love of his friends, but also due to being manipulated by Gwen, in a way contributes to his parents as well as nearly the entire Sky High student body being turned into babies and getting brainwashed by Gwen. While he's still able to save the day with the help of his friends and get his happy ending, one has to admit he gets put in some stressed circumstances.


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