The characters of the 2005 Disney superhero film Sky High.
- All of the Other Reindeer: It's tradition for the "Hero" class students to dunk on the "Sidekicks," which the Sky High administration seems to tolerate.
- Color-Coded Characters: Each one has a color or two they primarily wear, and together the seven main kids form a complete rainbow.
- Fantastic Caste System: Sky High enforces a system called "Power Placement" whereby people with traditionally cool powers become superheroes and people with "useless" powers are stuck as Sidekicks.
- Incompletely Trained: Well, yeah, they're still in high school.
- Ordinary High-School Student: Most of them, just with the addition of superpowers.
- What Kind of Lame Power Is Heart, Anyway?: This question is the bane of the Sidekicks' existence.
- Wise Beyond Their Years: Many of them raise some very good points about how the school is run that the adults don't listen to.
William Theodore "Will" Stronghold
Son of the two highest-ranking superheroes in the world, the Commander and Jetstream, fourteen-year-old Will begins his freshman year at his parents alma mater with big shoes to fill and, to quote him, one small problem he has no superpowers whatsoever. Though hes concocted elaborate ruses to convince his parents hes inherited his fathers super strength, his powerlessness is laid bare before the whole school and he ends up stuck in the inferior Sidekick track along with his best friend Layla. From there, he befriends fellow sidekicks Zach, Ethan, and Magenta, falls for the lovely Gwen (while remaining oblivious to Laylas own feelings for him), and makes a quick enemy of Warren Peace, son of his fathers nemesis, a confrontation with whom reveals he might not be as helpless in the world of superhumanity as he seems.
- Adorkable: A typical gawky teenage boy. Even during the final battle, he's improvising pretty much everything.
- All-Loving Hero: He helps people for a living as a high school student.
- Betrayal by Inaction: After he manifests his powers and starts dating Gwen, the popular crowd conspires to keep him away from his Sidekick friends. He's clearly uncomfortable, but he doesn't question it either until they make Layla cry and throw a party in his house without permission.
- Beware the Nice Ones: During his first encounter with Warren, he tries to defuse the situation peacefully. When that doesn't work, he gets chased down until Warren threatens his friends. This angers Will enough to lift the table Warren is on and punch him through a wall, though he looks no worse for wear.
- The Call Put Me on Hold: When Warren threatens his friends in the cafeteria, he manages to manifest his Super Strength. Later, he gains his mother's flight when Royal Pain nearly kills him.
- Childhood Friend Romance: With Layla. They've been best friends since the first grade.
- Color-Coded Characters: Red, white, and blue, like his parents. In the main cast rainbow, he's the "blue."
- Cool Loser: Pretty good-looking and definitely has less loser qualities than his friends, and is the son of two famous superheroes. However, due to his initial lack of powers and the fact that sidekicks are ostracized at Sky High, he starts as one at the beginning of the film. He does become popular after gaining powers and it sticks after he saves the school.
- Corrupt the Cutie: Definitely endearingly awkward, and he nearly abandons the things that matter to him after becoming popular. He pulls himself back.
- Crush Filter: When he looks at Gwen, the focus becomes softer and the '80s song "True" starts to play.
- Love Triangle: At the center of one, with Gwen and Layla as the "angles."
- Meaningful Name: Will as in willpower, Stronghold as in Super Strength.
- Morality Chain: Layla is this to him. When Gwen makes her cry at the party, he breaks up with her on the spot, despite not even knowing exactly what she said, and throws all the popular kids out of his house.
- Muggle Born of Mages: Starts the story as this, but gains Super Strength later on and eventually flight, as well.
- Nice Guy: A level-headed and nonviolent kid, who always tries reasoning with his enemies before fighting.
- Non-Action Guy: Despite wielding Super Strength, he'd much rather talk out his differences with his enemies than fight. Shame he keeps pressing their Berserk Buttons.
- Official Couple: Gwen is his love interest. But when that relationship sinks, he starts a new one with his longtime admirer Layla.
- "Scooby-Doo" Hoax: He concocts elaborate ruses to make it seem like he has powers at first, so he doesn't have to tell his parents he's powerless.
- Stock Superpowers:
- Super Strength: Inherited from his father, and manifested when Warren threatens his friends during their fight.
- Flight: Boomer tries to test to see if he's inherited this from his mother, which just gets him launched into a hard pillar and injured. Gains it for real at the end when Gwen tosses him off the edge of the school.
- Superpowerful Genetics: Will inheriting both his parents' powers is an anomaly. The children of two super parents usually inherit one or the other, or neither — never both.
- Took a Level in Badass: As it turns out, he does have powers, he just lacked a sufficient stressor to awaken them. He gains Super Strength about a quarter or so into the film and Flight as an 11th-Hour Superpower during his Final Battle with Royal Pain.
- Unfazed Everyman: As a "normal" person growing up among super humans, he's amusingly nonplussed by the weirdness surrounding him.
- Unskilled, but Strong: When he gains his strength, his lack of experience in direct combat shows. While his blows are powerful, Will lacks sufficient technique to make his hits really count.
Wills neighbor and best friend since first grade, Layla is an impassioned feminist and environmental activist who starts Sky High along with him. Shes an extremely powerful chlorokinetic, but her refusal to submit to the schools Power Placement system lands her in the Sidekick track along with the seemingly powerless Will. She also suffers from angsts of a considerably more mundane form namely long-harbored feelings for her best friend that shes too shy to tell him about, which in turn leads her by chance to an unlikely friendship with Wills rival Warren, who encourages her to speak up.
Her mother is a heroine who can speak to animals and her father is a normal human.
- Almighty Janitor: She's one of the most powerful kids in the school, but gets shunted into Sidekick class for refusing to show Boomer her power. She also most likely refrained from showing her full power up until Homecoming — when Will finally awakened his super strength he was moved to the Hero track. If Layla had done the same, she would've been moved up along with him.
- Badass Pacifist: When she uses her powers, Layla only immobilizes her opponent despite being significantly more powerful. Layla states she doesn't believe in using her powers unless the situation demands it.
- Betty and Veronica: Betty (the sweet Girl Next Door Childhood Friend) to Will's Archie and Gwen's Veronica.
- Color-Coded Characters: Green, naturally, which is her color in the main cast rainbow.
- Corrupted Character Copy: Inverted. A passionate environmentalist Redhead In Green with a Green Thumb? She's a good Poison Ivy.
- Curb-Stomp Battle: Once she's provoked into using her powers on them, Penny and her clones go down instantly.
- The Cutie: A sunny, pretty, and kind teenage girl.
- Deuteragonist: The story's second most important character, with her own mundane arc of dealing with the Love Triangle she's stuck in, contrasting Will's more fantastic main plot.
- Earn Your Happy Ending: Does she ever. She defeats one of her prominent bullies, in the process proving she has Hero-worthy powers, confesses her feelings to Will, who reciprocates, and gets to share a Homecoming dance with him in midair.
- Godwin's Law: Says Power Placement "sounds fascist."
- Granola Girl: A passionate environmentalist, to the point she moves other people's recyclables from the trash bin if they're thrown away. She's not mocked by the narrative for it, though.
- Heroes Want Redheads: A red-headed love interest for the main character.
- Hollywood Nerd: Pretty variety, of course.
- Love Triangle: Stuck on the losing end of one, much to her chagrin. She pulls through.
- Morality Chain: She is this to Will, to the point that he breaks up with Gwen and throws all the popular kids out of his house once they make her cry, without even knowing the exact context of the altercation.
- Morality Pet: She's this, meanwhile, to Warren, as she uses him as a sounding board for her problems, leading to him taking a shine to her and gradually shedding his tough guy exterior for her.
- The Not-Love Interest: Warren is this to her. She pours out her angsts over her datelessness to him, and by interacting with her, he becomes less of a sourpuss and eventually befriends the main gang. The two are so integral to each other's Character Development that many fans feel the "not" part is debatable.
- Official Couple: After much suffering, she does finally end up with Will.
- O.O.C. Is Serious Business: She definitely senses something is very wrong when she sees that her kind, humble best friend seems to be throwing a Wild Teen Party at his house.
- One-Woman Army: A pacific ecample. Able to stop and immobilize Penny and six of her clones.
- Operation: Jealousy: She and Warren hit on the idea to pretend to date to annoy Will, her to make him jealous, him... to annoy Will.
- Pre-Asskicking One-Liner: Poor Penny.
- Layla: Big Mistake.
- Redhead In Green: Often wears green clothes to contrast with her fiery red hair.
- Shout-Out: There's been speculation that she's named for Laurey Williams, the heroine of Oklahoma!. Not only do their names sound similar, but the show is mentioned in the movie in the context that the future Commander and the future Baron Battle fought over the male lead role of Curly, Laurey's love interest, while they were at Sky High - and Layla's own romantic prospects happen to be the two men's sons. For bonus points, Laurey is also involved in a love triangle (though she's the one in the middle) and the show also includes a character named Will who is involved in a completely different B-plot love triangle.
- Stock Superpowers:
- Green Thumb: A very strong chlorokinetic, to the point where she defeats a senior Hero effortlessly.
- Unlucky Childhood Friend: It's not known how long she's been crushing unrequitedly on Will for, but it's implied to have been a long time. Her patience pays off in the end.
- You Wouldn't Like Me When I'm Angry: She doesn't believe in using her powers unless the situation demands it. However, piss her off to the point where she's willing to use them and she's terrifying.
Gwendolyn "Gwen" Grayson
Sky Highs glamorous student council president, head of the homecoming committee, and all-around most popular girl in school, Gwen is a powerful technopath and a senior Hero. Shes normally a kind person, but is known to be somewhat insensitive to the suffering of students on the Sidekick track. Will falls hard for her, and she reciprocates after his fateful confrontation with Warren, but the popularity his newfound relationship brings drives a wedge between him and his Sidekick friends, and he soon learns that like many seemingly-ideal people, Gwen is a woman of plentiful secrets.
Her mother is a deceased heroine with the same powers and her father a retired sidekick.
- 100% Adoration Rating: To Will, she's a goddess, and it's implied most of the school sees her the same way.
- Affably Evil: She acts very friendly towards Will. Too bad she was a supervillain all along.
- Betty and Veronica: Veronica (high-status, secretive, and alluring) to Will's Archie and Layla's Betty.
- Bitch in Sheep's Clothing: Not just any old bitch, but an outright supervillain.
- Brainy Brunette: A dark-haired technopath.
- The Charmer: A very pretty and charismatic young lady.
- Color-Coded Characters: Pink, light purple, and white. The "violet" in the main cast rainbow.
- Evil Cannot Comprehend Good: In a manner; she is genuinely caught off guard by Will's integrity to stand by his Sidekick friends instead of dropping them to join the popular crowd. It probably has to do with the fact she was a branded a loser when she went to Sky High the first time.
- Evil All Along: She's not as affable as she appears to be.
- Even Evil Has Standards: Implied. Instead of killing the herpes, which is what the audience would expect her to do, she turns them into babies instead. Her non-bloodlust could have something to do with how she was originally trained to be a good guy.
- FaceHeel Turn: As Sue Tenny, Gwen was once a hero-in-training at Sky High until she got written off as a science geek, which causes her to enact her Evil Plan.
- Freudian Excuse: Due to being relegated to sidekick status, Sue became an evil supervillain bent on turning all the superheroes into infants.
- Good Smoking, Evil Smoking: Steve mentioned that Sue Tenny was rumoured to have been smoking in the girl's bathrooms.
- Has a Type: For those with Super Strength, it appears. Considering the fact that The Commander was implied to bully her in the past, yet Gwen referred to him as "My dear Commander", and Will just so happens to also have Super Strength... Yeah.Layla: He's strong...!Gwen: He's super strong~
- In Love with the Mark: Possibly. She takes Will breaking up with her very badly, even though she already had the Pacifier by that point, indicating she actually intended on keeping him around afterwards; what her endgame plan for him was is never revealed. She also looks genuinely worried when Will takes a nasty hit from Speed during Save the Citizen.
- Innocently Insensitive: Once she and Will start dating, several of her actions seem to discourage his Sidekick friends from continuing to hang out with him, whether she notices she's doing it or not. Though it's likely not so innocent in reality.
- Lovable Alpha Bitch: Popular and occasionally inadvertently rude, but generally a pleasant person. Later revealed to be far worse than even a standard Alpha Bitch.
- Love-Interest Traitor: The hero's girlfriend is the Big Bad? Who'da thunk?
- Missing Mom: Died when she was a baby. Probably.
- Ms. Fanservice: We get to see her in a backless tank top and a very low-cut Homecoming gown.
- Nice Job Fixing It, Villain!: If Gwen hadn't made Layla cry at the Wild Teen Party at Will's house (which itself isn't this since she needed a good distraction to get her hands on the Pacifier), Will would have gone to the dance with her and been incapacitated with the other heroes. Will by staying at home only to arrive later with Ron defeats her in battle and helps save the school.
- Official Couple: She is Will's love interest. As one might tell from some of these other tropes, it goes pear-shaped.
- Peerless Love Interest: Will sees her as his ideal partner, to the great irritation of his best friend Layla.
- Pet the Dog: She fixes the Strongholds' garbage disposal, seemingly without any villainous reason to do so.
- Pink Means Feminine: Definitely the girly-girl of the cast, and dresses mainly in various shades of pink.
- The Reveal: Gwen's hiding quite a few things from the world at large, and they're revealed like peeling back the layers of an onion. She first reveals she's Royal Pain, then she speaks in Patrick Warburton's voice, revealing she's the cloaked mastermind as well, and is finally unveiled as the original Royal Pain, Sue Tenny, reborn.
- Sexy Backless Outfit: Wears a backless tank top to the party she throws, where she really ratchets up her seduction of Will.
- Shout-Out: Gwen Stacy, an iconic superhero love interest, and Dick Grayson, an iconic sidekick. Gwen is a hero's love interest and, as a villain, is motivated by the fact that she, or rather Sue Tenny, was stuck in sidekick class and bullied at Sky High.
- Statuesque Stunner: The tallest of the girls, and considered the most attractive. She's even noticeably taller than her boyfriend Will.
- Stock Superpowers:
- Technopath: Provides the name and the page image, though the power did exist previously.
- Student Council President: Her role at Sky High.
- The Ugly Guy's Hot Daughter: Her surviving parent is her father, who is shown to be a short and weedy balding man sporting Nerd Glasses, while Gwen herself is a bombshell.
- Walking Spoiler: If those white spaces didn't tip you off, she's subject to the biggest twist of the kids.
- Western Terrorists: She tries to drop the whole school onto the city below and kill millions in a terrorist attack as a further insult to superheroes who's families she just abducted to be raised as villains.
- Woobie, Destroyer of Worlds: Raised all her life by a crazed Villainous Harlequin to be the instrument of a decades-spanning revenge scheme - not hard to see why she's a bit off her gourd, no?
A pyrokinetic sophomore (probably, see below) Hero at Sky High, Warren is the schools resident pariah, for one very simple reason his father, Baron Battle, is one of the worst supervillains to ever live. Solitude suits Warren just fine, however, as he doesnt like much of anyone else, either. Their fathers animosity makes him a quick enemy of Will, but he shows his softer side when he stumbles upon a dejected Layla while working at his part-time job at a Chinese restaurant and strikes up an Odd Friendship with her, helping her deal with her issues as she helps him come out of his shell.
- All of the Other Reindeer: He is considered an academic pariah due to his father being one of the most despicable supervillains.
- The Aloner: Seems to enjoy solitude (to the extent he enjoys anything), to the point that he discourages others from sitting at his lunch table.
- Anti-Hero: Definitely a darker character than the other main kids, but by no means an actual villain.
- Berserk Button: As mentioned above, do not mention his supervillain dad.
- Color-Coded Characters: Red and black. The "red" in the main cast rainbow.
- Cool Loser: Despite being Tall, Dark, and Handsome, having a cool demeanor, and being part of the hero program, he's a social outcast. Being the son of a hated supervillain can do that to you.
- Fire-Forged Friends: By the end of the film, he and Will are best friends thanks to all they've been through together.
- The Gadfly: Has shades of this at times. He actually has no stake in the Will-Layla-Gwen love chutzpah, but agrees to Layla's fake relationship idea just to mess with Will's head.
- Hair-Trigger Temper: He gets extremely angry with minimal provocation and usually deals with it by using his superpowers.
- Loser Son of Loser Dad: Despite being in Hero class, he's ostracized at school due to everyone being worried he'll turn out like his father. He seems to enjoy solitude, though.
- Jerk with a Heart of Gold: His introductory scene has him attempt to utterly annihilate Will, but as the movie progresses, it's shown that he's not such a bad guy after all.
- Meaningful Name: A corny but pretty cool example nonetheless—his father was an infamous supervillain, his mother was a powerful hero. He's the product of war and peace.
- Misunderstood Loner with a Heart of Gold: He's actually nothing like his dad, not that anyone gives him the chance to prove it.
- Morality Pet: Layla serves as this to him, as he gives her relationship advice and she becomes the first person he genuinely seems to like. He also tries to protect her several times during the final battle.
- Mr. Fanservice: A hunky, Tall, Dark, and Handsome teenage boy played by an ex-model. The director himself said he was intended to be a character teen girls in the audience would fall for.
- Perpetual Frowner: Rarely seen without his trademark scowl, at least until he meets Layla.
- Pet the Dog: Any of his interactions with Layla, at least before the climax, where he shows he truly was Good All Along.
- Punny Name: Get it, War and Peace?
- Red Herring: The film's marketing played him up as the probable Big Bad, which is very far from the truth.
- The Rival: Is initially this to Will, due to their fathers' animosity.
- Series Continuity Error: While his school year is never actually stated in the film, the supplemental materials disagree on whether he's a freshman or a sophomore. Sophomore is generally assumed because he doesn't go through Power Placement with the other incoming freshmen.
- Sins of Our Fathers: Everyone at Sky High considers him a pariah, given his father was a supervillain.
- Skunk Stripe: Has a streak in his hair dyed red.
- Ship Tease: With the unnamed ice-controlling girl at the end. To be frank, it's a fitting match.
- Stock Superpowers:
- Playing with Fire: He's a pyrokinetic.
- Tall, Dark, and Handsome: The second tallest character (after Zach), and very attractive and brooding.
- When He Smiles: Watch him light up when he agrees to Layla's Operation: Jealousy plan.
- White Sheep: The good son of a famous villain.
Zachary "Zach" Braun
Yet another freshman Sidekick, Zach is a previous acquaintance of Will and Layla whose only power is glowing in the dark. Despite the limited utility his ability provides, Zach is a confident and good-hearted (if a bit dim) young man who believes he will be a great hero one day, even with all the world telling him otherwise. His closest friend, and possibly more, is Magenta.
- All There in the Manual: His last name isn't mentioned in the movie itself.
- Beta Couple: His relationship with Magenta develops in the backdrop of the stormy Will-Gwen-Layla triangle, and from what we see of it, which admittedly isn't much, it has a lot less drama to it.
- Butt-Monkey: He's subject to the most physical comedy of all the characters in the movie.
- Cloudcuckoolander: Very eccentric, and not what you'd call smart, but lovable all the same.
- Color-Coded Characters: Neon yellow and white. The "yellow" of the main cast rainbow.
- The Danza: Nicholas Braun as Zach Braun.
- Huge Guy, Tiny Girl: He's the tallest guy, and he's interested in the shortest girl, Magenta.
- Implied Love Interest: Technically speaking it's never explicitly stated he and Magenta are an item, but it's very strongly insinuated.
- Large Ham: Really loves to talk about how amazing his power is, even though it... isn't.
- Light Is Good: Can glow in the dark, and is one of the heroes.
- Non-Action Guy: One of the few characters in the movie with no combat capability at all.
- Pretty Fly for a White Guy: Has this fashion choice and behavior at various points.
- Shirtless Scene: Part of his physical comedy is not being able to change fast enough from regular clothes to gym clothes.
- Stock Superpowers:
- Light 'em Up: A very, very weak version - all he can do is glow in the dark.
- Super Zeroes: Even by Sidekick standards his power is pretty unimpressive, and he contributes the least to the final battle even with Plot Tailored to the Party in full effect.
A cynical and gothy freshman Sidekick, Magenta meets Will and Layla on the bus to Sky High along with Ethan and quickly becomes part of their circle of friends. Her power is shapeshifting, with an unfortunate twist shes limited to the form of a purple guinea pig. She resents her Sidekick placement but is virtually unfazed by everything else, including staring down Warren Peace, and shares a special bond with Zach.
- All There in the Manual:
- The official website says her nickname is "Maj," but it's never actually used in the film.
- Like Zach, her last name isn't mentioned either.
- Amazing Technicolor Wildlife: Her guinea pig form has purple highlights on its fur, to match her color scheme.
- Badass Adorable: A cute goth girl who has the power to transform into a guinea pig and that power proves to be useful near the end.
- Color-Coded Characters: Despite her name, dark purple and black. The "indigo" in the main cast rainbow.
- Deadpan Snarker: Always on hand to offer some cynical humor pertinent to whatever's going on at the moment.
- Goth: Snarky, cynical variety rather than perky.
- Heart Is an Awesome Power: She really pulls through at the climax, when she has to go down a tiny duct to fix the school's sabotaged anti-gravity device.
- Implied Love Interest: As stated in Zach's entry, she's this to him. They even take each other to Homecoming, on the basis that they both hate Homecoming.
- Magic Pants: Her clothes shapeshift with her, and seem to take the form of a purple streak in her guinea pig form's fur.
- Opposites Attract: The snarky shapeshifting goth has a thing for the bright, hammy glowing kid.
- Stock Superpowers:
- Animorphism: Limited to a purple guinea pig.
- Ridiculously Cute Critter: Her other form is a guinea pig. Enough said.
- Wire Dilemma: Has to chew through the right wire to shut off the device Royal Pain used to sabotage the school's anti-gravity generator. All the wires are red, but she does manage to find the right one.
The last of Wills quartet of friends, Ethan is a bright freshman Sidekick who first meets him on the bus along with Magenta. His power is melting into a mobile puddle of orange liquid; Coach Boomer is less than impressed. When it comes to established superheroes hes something of a fanboy and a suck-up, and is a frequent target of Lash and Speeds bullying. To say hes a total wimp, however, would be a gross oversimplification, and he possesses a legitimate drive to be a great hero.
- Adorkable: Even in comparison to Will, he's awkward, and all the more endearing for it.
- All There in the Manual: Like Zach and Magenta, his last name isn't mentioned in the movie.
- Black and Nerdy: Complete with big Nerd Glasses.
- Bring My Brown Pants: Spontaneously melts during the cafeteria fight when staring down an enraged Warren, in what seems to be a reference to this trope.
- Butt-Monkey: A much more Played for Drama example than Zach, as he's the target of serious bullying by Lash and Speed.
- Color-Coded Characters: Orange and while, like a creamsicle. The "orange" in the main cast rainbow.
- The Dog Bites Back: After being tormented by Lash and Speed the whole movie, he gets his revenge when they reveal themselves as villains during the climax. He dunks Lash's head in the toilet, just as Lash had done to him earlier, and slips up Speed to enable Warren to take him out.
- Fanboy: Of established heroes, such as the Commander and even Sonic Boom.
- Heart Is an Awesome Power: For instance, melting enables you to set up a sneak attack on a more traditionally-powerful super-being. Lash never saw him coming.
- Motor Mouth: Tends to get quite talkative when meeting an older hero.
- Professional Butt-Kisser: Has a tendency to suck up to higher-ranked heroes, even Speed and Lash when they're tormenting him.Coach Boomer: So that's your power? Butt-kissery?
- Stock Superpowers:
- Making a Splash: Like Zach, a very weakened take on the classic power: all he can do is melt into a puddle that can move.
- Took a Level in Badass: He seems to find some new ways to use his powers over the course of the movie, such as the ability to flow ''vertically', enabling him to take down Lash.
Sky Highs second most popular student, Penny is a senior Hero and a self-duplicator whose clones comprise the Sky High cheerleading squad in its entirety. Shes a distinctly less pleasant person than her best friend Gwen, and though she tolerates Will after he and Gwen hook up, she plays a significant role in isolating his friends in Sidekick class from him.
- Acting for Two: Inverted; she's played by twin sisters.
- Alpha Bitch: An attractive, arrogant cheerleader who loathes everyone lower than her on the high school pecking order.
- Black Best Friend: Has this role to Gwen.
- The Cheerleader: Thanks to her power, she's Sky High's entire cheerleading squad.
- The Dragon: Gwen's primary muscle in her evil scheme.
- Fantastic Racism: Loathes "Hero Support" and, really, anyone less popular than she is.
- Hate Sink: Quite possibly the only character in the film without a single redeeming quality. She proves her Hate Sink mettle being being the prime mover of Will's isolation from his friends.
- Jerkass: She's an exceptionally unpleasant and bigoted person.
- Jerk with a Heart of Jerk: Unlike Warren, she truly is rotten to the core, and proves it by joining her BFF Gwen's squad of villains.
- Meaningful Name: Her name is probably a play on idioms and phrases containing the word "penny" such as "If I had a penny for every time I X...", or, "Worth every penny", etc., considering her self-duplication power.
- So Long, Suckers!: Locks the attendees of the Homecoming dance in the gym to be Pacified, and blows a condescending kiss at them as she leaves.
- Stock Superpowers:
- Me's a Crowd: She's a self-duplicator who's an entire cheerleading squad unto herself.
Lash and Speed
The thin Lash and portly Speed are Sky Highs resident bullies and Jerk Jocks, with the power of elasticity and super speed respectively. Theyre Hero-class seniors, but are hardly heroic people - Ethan and Zach are favorite targets of theirs (though they pick on pretty much anyone, even teachers), and they also happen to be undefeated players at Save the Citizen, one of Sky Highs sports of choice, in which they, rather worryingly, always choose to play for the Villain team.
- Acrofatic: Speed may be overweight, but that doesn't stop him from being an effective user of his power.
- Bavarian Fire Drill: One of the hustles they're seen performing is extorting money from incoming freshmen by posing as the "Sky High Welcoming Committee."
- The Bully: Classic variety, with swirlies, stuffing into lockers, and so on.
- Card-Carrying Villain: They always play for the "Villain" team in Save the Citizen, leaving it little surprise when they turn out to actually be villains.
- Fat and Skinny: Speed and Lash, respectively.
- Finishing Each Other's Sentences: They do this on occasion.
- Fat Bastard: Speed is a nasty, overweight guy.
- Hate Sink: Along the same lines as Penny, they don't get much in the way of positive traits. Even Layla laughs when they get hurt in gym.
- Jerkass: They even bully Mr. Boy and Ron, who are staff members.
- Jerk Jock: Though they don't fit the usual super-muscular physical type, they're Sky High's best Save the Citizen players, and don't you ever forget it.
- Jerk with a Heart of Jerk: Like Penny, there's really nothing good about them, and they prove it by joining Gwen's coalition of villains at the end.
- Kick the Dog: More or less everything they do, but one example sticks out: while playing Save the Citizen against Will and Warren, speed repeatedly runs in circles around Warren, creating a vortex to suck away his oxygen, which both snuffs out his flames and renders him unable to breathe, nearly killing him.
- Lack of Empathy: Speed and Lash seem to care about nothing and no one except possibly each other. They even pick on the teachers. And depending if Speed knew what he was doing to Warren during Save the Citizen, it's entirely possible they're okay with casual murder.
- Lean and Mean: Lash is a nasty thin guy.
- Nice Job Fixing It, Villain!: Lash made a big mistake in tripping Will so that his lunch spills over Warren Peace. The ensuing fight leads to Will discovering his super powers, which he later uses to literally tie up Lash into a knot during Save The Citizen.
- Only Known by Their Nickname: Speed and Lash are the only names they ever get; even teachers call them that.
- Shot in the Ass: When Ethan makes Speed slip during the climax, Warren throws a fireball at his butt, causing him to crash headfirst into a wall.
- Shout-Out: We briefly see that Lash has a drawing in his locker that looks a lot like the Dark Mark.
- Stock Superpowers:
- Too Fast to Stop: Speed's Achilles' Heel, and how he's defeated both at Save the Citizen and at the climax.
- Troll: Provoke Will into a fight with Warren just for amusement, then ensure the two are paired up against them for Save the Citizen.
- Adults Are Useless: They're really not very competent at all, and never listen to what the kids have to say for the most part. Ironically enough, the most competent adult is the bus driver.
- Cloudcuckoolander: The adult men are all extremely eccentric, the women to a lesser extent.
- Rude Hero, Nice Sidekick: The Sidekicks are far more pleasant than the Heroes by and large.
Steve Stronghold/The Commander
The most successful superhero in the world, Steve Stronghold is the Commander, wielding the powers of super strength and invulnerability, Josies husband, and Wills father. He wants nothing more than for his only child, Will, to join him on the battlefield, and with this pressure bearing down on him, Will take steps to convince his father hes inherited his powers. Hes not always the most intelligent or tactful person, but he does love his son and eventually learns to accept him, powerlessness and all. His civilian identity is as the most successful realtor in the city of Maxville, along with his wife.
- The Ace: The most powerful and popular superhero in the world! Still needs his kid to save him at the climax, though.
- Action Dad: He's one of the most popular superheros in the world and only wants his son to follow in his footsteps.
- Alliterative Name: Steve Stronghold.
- Arch-Enemy: Had one in Baron Battle, who he shipped off to four consecutive life sentences. It's not stated if he has one particular nemesis in the present.
- Battle Couple: With his wife.
- Big Good: Seems to be this for the superhero community at large.
- Bumbling Dad: He is most certainly not the brains of the Stronghold household, though he's apparently a legitimately good real estate agent.
- The Cape: A stereotypical superhero, complete with actual cape.
- Color-Coded Characters: A very patriotic red, white, and blue, shared with his wife and son.
- Condescending Compassion: Has shades of this toward Will's friends.
- Curb-Stomp Battle: Royal Pain defeats him at Homecoming with one blast of the Pacifier.
- Does Not Know His Own Strength: Particularly when he's mad - he keeps a large number of identical phones for when he presses the buttons too hard.
- Dumb Muscle: He didn't know Royal Pain was a girl. Although he might have meant he didn't know she was young.
- Good Parents: As disappointed as he is with Will's placement in the Sidekick community, he truly does want what's best for his son and tries to be as supportive as he can.
- Innocent Bigot: He shows some passive prejudice against sidekicks, possibly inherited from his own father who is never seen and may be deceased. He wises up by the end of the movie.
- Large Ham: He has quite the ego on him, though he's mostly a good guy.
- Legacy Character: Inherited his superhero career from his father, and plans on passing his own down to Will.
- Reformed Bully: If one pays close attention, there are several hints that he was a bully during his Sky High days, and that one of his victims was Sue Tenny, the future Royal Pain. In the present, the worst he is is an Innocent Bigot.
- Shipper on Deck: Seems to be shipping his son with Gwen. It costs him.
- Steven Ulysses Perhero: Steve Stronghold has Super Strength.
- Stock Superpowers:
- Superman Substitute: He seems to be this for the setting — he is a stereotypical upright and patriotic superhero widely considered to be the best, and has the powers of super strength and near-invulnerability. (He can't fly, though.)
- Unstoppable Rage: He really loses his temper when he thinks Boomer intentionally flunked Will out of Power Placement to spite him, though to his credit he does not take it out on his son.
- Unwitting Instigator of Doom: He and Josie inviting Gwen to dinner turns out to be the impetus for everything that goes wrong in the film, both the mundane and the fantastic.
Josie DeMarco Stronghold/Jetstream
The more intelligent half of the Stronghold power couple, Josie is the worlds second most successful hero under the codename Jetstream, with the power of supersonic flight and an expertise in martial arts as well. She tries her best to rein in both her husbands eccentricities and her sons teenage angst, and is more accepting of his powerlessness than Steve is.
- The Ace: Along with her husband, though she's humbler about it.
- All There in the Manual: Her maiden name, DeMarco, is spoken only in the alternate opening seen on the DVD.
- Amazingly Embarrassing Parents: Josie has a bit of habit of babying Will, much to his embarrassment. Before leaving for school, she talks about embarrassing moments from Will and Layla's childhood and worries about his first day of school while she and Steve are fighting crime.Jetstream: Are you sure he'll be okay? What if he forgets his lunch?Commander: Josie, Josie, you've got to stop babying the boy.
- Battle Couple: With her husband.
- Curb-Stomp Battle: Goes down instantly to the Pacifier right after her husband.
- Good Parents: Josie is much more accepting of Will's lack of powers and cares more about his life as a whole. This is best shown that even after learning that her son inherited his father's strength, she is still cross at him for getting in a fight that nearly destroyed the cafeteria.
- Hidden Depths: She's mentioned to be a pinball aficionado, and there's a machine themed after her and her husband in the Sanctum.
- Ms. Fanservice: As seen above, her costume strongly emphasizes her cleavage.
- Only Sane Man: As mentioned, she tries to keep a lid on all the weird things that go on in the Stronghold house.
- Satellite Character: Isn't nearly as important to the story as her husband is.
- Stock Superpowers:
- Unwitting Instigator of Doom: She and Steve inviting Gwen to dinner turns out to be the impetus for everything that goes wrong in the film, both the mundane and the fantastic.
- Women Are Wiser: It's stated she handles the scientific side of the Strongholds' superhero career, and also acts as a voice of reason to her husband and son.
Sky Highs head teacher, with the ability to transform into a ball of light. Shes first seen introducing the freshmen to the school prior to Power Placement, and also shunts Will and Warren off to detention following their fateful cafeteria brawl. Probably the most normal of the Sky High staff seen, shes long since been desensitized to the wackiness of her subordinates.
- Actor Allusion: At one point says "I'm not Wonder Woman", alluding to Lynda Carter's best-known role.
- Adults Are Useless: She's pretty ineffective at regulating both the Hero-Sidekick tensions and actual supervillain attacks.
- Ambiguously Human: According to her profile◊, she was the one who created the Grand Canyon. Either this means the Grand Canyon in this universe was created very recently by Principal Powers, or her powers give her the Longevity Treatment, or she's Not Quite Human. Her power being named "Astro Comet" might hint at the fact that the latter is correct.
- Big Good: As the highest-ranked teacher in the story, though she doesn't really do much.
- Casting Gag: Lynda Carter is best known for playing Wonder Woman in the 1970s TV series.
- More Expendable Than You: She gets Pacified at the climax because she wants to get the kids out of the gym first.
- Ms. Exposition: Her opening speech informs the incoming freshmen about the school and Power Placement.
- Reasonable Authority Figure: She's not a bad person and cares about her students, though she's definitely willing to discipline them.
- Shout-Out: After resisting it the entire movie, she says "I'm not Wonder Woman, you know" while chiding the imprisoned villain kids for their actions, as a doffing of the hat to Lynda Carter's most famous role.
- Stern Teacher: Has shades of this when sticking people in detention, understandably.
- Stock Superpowers:
- Voluntary Shapeshifting: Into a ball of light called an "astro comet" on the film's website. According to her profile, it's an actual comet.
- What a Senseless Waste of Human Life: Nobody actually dies, but she says something similar to this when chiding the villain kids for throwing away all their potential at the denouement.
Jonathan Boy (formerly All-American Boy)
Formerly All-American Boy, sidekick to The Commander, a now thoroughly past his prime Jonathan Boy is the homeroom teacher to the freshman Sidekick class. Seemingly completely forgotten by his old partner, to the point that Will didnt even know he existed, Mr. Boy tries his best to spin the sidekick profession as a noble trade, but is transparently sad, lonely, and insecure. His powers are unknown, but according to him he still does a little freelance.
- Butt-Monkey: Falls victim to a lot of slapstick, including being picked on by Speed and Lash.
- Camp Straight: He talks about superhero fashion and is generally kind of swishy, but he's also still pining away for Josie DeMarco, the prettiest girl in school.
- Comedic Sociopathy: Not as much as his pals Boomer and Medulla, but he seems to find the idea of using a real person rather than a mannequin for Save the Citizen amusing.
- Forgotten Fallen Friend: He's not dead, at least not physically, but he's definitely fallen on hard times and his old partner has nearly forgotten his existence. The alternate opening shows that Steve and Josie abandoned him, still tied up, after defeating Royal Pain.
- Kid Sidekick: Was billed as this despite being the same age as his hero. Poor guy.
- The Mentor: Takes on this role to the sidekick kids, with as much enthusiasm as he can muster (which isn't a lot).
- Riddle for the Ages: Just what is his power, anyway? And why does Steve barely remember him in the present?
- Sad Clown: He's pretty goofy, but it's a transparent mask for his numerous insecurities.
- Steven Ulysses Perhero: "Boy" is his actual last name.
- Super Zeroes: To an ever greater extent than Zach, as it's not apparent if he has any powers at all. The official website simply gives the evasive answer of "super-helpfulness." Unless they meant that literally.
- Undying Loyalty: Towards both Steve and Josie. Somewhat deconstructed too, as he worked very hard for both of them but neither seemed to appreciate him for it.
- Unrequited Love Lasts Forever: His high school crush on Josie hasn't gone away after thirty years.
- Unwilling Suspension: He and Steve were subject to this by Royal Pain in the alternate opening. Josie freed Steve but forgot about him.
- Utility Belt: Teaches his students how to use these.
Sky Highs deadpan, eccentric, and very, very mad science teacher, a superintelligent telepath with a literally swelled head. Hes friends with Mr. Boy and Boomer, is known to torment his students with green rocks, owns a jetpack instead of a car, and formally introduces Will and Gwen to each other when theyre paired up for his class, setting the stage for drama both mundane and fantastic.
- All There in the Manual: The official website says he's telepathic in addition to superintelligent.
- Berserk Button: Never confuse rays with beams in his class, or he'll freeze you solid.
- Brainy Baby: He retains his adult intelligence after being Pacified, which enables him to reverse the device's polarity and return everyone to their proper ages.
- Comedic Sociopathy: Let's see, he freezes underperforming students solid, exposes others to Green Rocks that make them faint, and agrees with Mr. Boy that subjecting a real person to Save the Citizen is a funny idea.
- Evil Is Sexy: Seems to be an in-universe believer in this; Boomer prods him into a double date by telling him the woman he's setting Medulla up with is his own date's Evil Twin.
- Green Rocks: Has some of these in his classroom that he torments his students with.
- Kavorka Man: Despite being a nerdy mad scientist with an enormous head, when the aforementioned double date is shown, he's not only being fawned over by the evil sister, but has stolen the good one from Boomer as well!
- Mad Scientist: Semi-benevolent. And "Mad Science" is actually a subject taught at Sky High, and he's the teacher.
- My Brain Is Big: Just see the picture. It's still the case in baby form.
- Odd Friendship: You wouldn't expect a quirky science teacher and a Jerkass coach to get along, but Boomer's his best bud.
- Stock Superpowers:
- Telepath: Stated to be one by supplemental materials, but never actually shown.
- Unwitting Instigator of Doom: You wouldn't think pairing up a new student with the girl he's sweet on for science class would lead to massive drama down the line, but that's exactly what happens when Medulla introduces Will and Gwen.
Tommy "Boomer" Boomowski
Formerly the C-list hero Sonic Boom, Boomers career of professional heroics didnt work out and now hes stuck teaching gym at his old alma mater, something he transparently resents. Hes in charge of Power Placement, whereby incoming freshmen are sorted into the Hero or Sidekick courses, and makes no secret of his distaste for the latter class. His best friend is Medulla, and his power is, as his name implies, a sonic scream.
- '80s Hair: He had a mullet in his yearbook photo.
- Comedic Sociopathy: Gives a little evil chuckle when things start getting painful during the Save the Citizen match.
- Fantastic Caste System: He's the face and enforcer of Sky High's rigged system.
- Fixing the Game: At least according to Steve, he's been known to deliberately send the children of more successful heroes to Sidekick class as a form of Revenge by Proxy.
- Hate Sink: Downplayed. As the face of the Hero-Sidekick prejudice that drives the story's conflict, he's definitely a detestable person. He turns out to have a more functional moral compass than the three bullies, though.
- Jaded Washout: There's a definite indication that his angst over his own failed superhero career drives much of his assholishness.
- Jerk with a Heart of Gold: Despite being a very bad teacher, with a resentment of both Sidekicks and heroes more successful than him, he cares about his students. Best demonstrated at the climax, where he rushes to protect the kids from Royal Pain and gets Pacified for his trouble.
- Large Ham: It's Bruce Campbell with sonic scream powers; could he be anything else? He doesn't even need the sonic scream to be hammy.
- Meaningful Name: Possibly unintentional, but in addition to being a reference to his power, his nickname might be a nod to the Baby Boomer generation, as opposed to Millennials like the protagonists, which fits with Boomer being the "face" of the film's generational conflict theme. He definitely gives off the boomer vibe as well.
- More Expendable Than You: Sacrifices himself against Royal Pain to buy the main kids time to escape.
- Odd Friendship: With Medulla, as outlined in his entry.
- The Resenter: Has shades of this toward Steve, and it's implied this is true toward many more successful heroes.
- Shout-Out: Much of his character would seem to be a reference to Bruce Campbell's Star-Making Role, Ash Williams, and his "Boomstick."
- Steven Ulysses Perhero: As seen in his yearbook photo, his real name is "Tommy Boomowski."
- Stock Superpowers:
- Make Me Wanna Shout: He has a sonic scream to go with his name.
- Unknown Rival: There are some hints he was this to Steve during their school days.
Sky Highs very elderly and quirky school nurse, with the power of X-ray vision. She patches up Will after Boomers attempts to test his nonexistent super strength and flight during Power Placement leave him maimed. She later explains to him how superpower genetics work, including the fact that sometimes a child of superhumans will never inherit powers.
- Cloudcuckoolander: The most eccentric of Sky High's female staff members by far.
- Cool Old Lady: The oldest member of Sky High's staff seen, to the point that she remembers the other adults when they were teens, and a helpful and quirky person.
- Deadpan Snarker: See the quote, which she accompanies by hitting herself on the head with her rubber mallet.
- Made of Iron: She's just a little old lady, but she apparently survived being accidentally kicked through a wall by the Commander when he was in school...
- Meaningful Name: Her last name, Spex, is a Double Meaning. "Spex" as in specks and spectacles.
- Ms. Exposition: Explains Superpowerful Genetics to Will while he's in her office.
- Nerd Glasses: A very large, round pair that make her look rather goofy.
- Stock Superpowers:
- X-Ray Vision: Which is definitely helpful in her line of work.
Ron Wilson, Bus Driver
Ron Wilson, Bus Driver is, as his name implies, a Sky High bus driver, one of a handful of highly qualified individuals provided with the schools secret location and permitted to drive its state-of-the-art flying buses. Hes also a very rare genetic anomaly a child of two superhumans born with no powers whatsoever. As such he makes quick friends with Will, to whom he provides a business card and the option of his time whenever Will wants. Like Mr. Boy, Ron has some hints of resentment at his low station, but for the most part he takes genuine pride in what is legitimately a very important job.
- Almighty Janitor: On paper he's "just" a bus driver, but by nature of the sort of bus he drives he's also an accomplished pilot. Handy to have around in a fight, too.
- Berserk Button: Never ever under any circumstances drive a Sky High bus if you are not a qualified Sky High bus driver. Ron's fist will make close contact with your face, as Stitches finds out.
- Chekhov's Gun: Ron gives Will his business card on his first day of Sky High. Will uses it at the climax to summon him to race to the rescue after he figures out the villains' plan.
- The Chosen Many: He describes the Sky High bus drivers, of which he's the only one we see, in this way.
- Curb-Stomp Battle: Knocks Stitches' lights out in one hit.
- Fanboy: Of the Commander and Jetstream, which he transfers to their son.
- I Just Want to Be Special: Thanks to being a Muggle Born of Mages, he actively seeks out opportunities to be a hero. He gets his chance in the epilogue, compliments of a vat of toxic waste.
- Jumped at the Call: He's actively looking for calls to jump at, but the world hasn't quite obliged him yet.
- Muggle Born of Mages: His parents were both super humans, making his powerlessness a genetic anomaly. In fact, he's the only such example Nurse Spex has ever encountered in her long career.
- Nice Guy: Quite possibly the nicest in the cast.
- Nice Hat: Sports a cool Sky High bus driver hat, which Speed and Lash steal from him at one point and drop into a muddy puddle.
- Older Sidekick: Fills this role to Will.
- Sad Clown: Not as pronounced as Mr. Boy, but there are definite hints his enthusiasm for his station in life is a mask for insecurity with it.
- Stock Superpowers:
- Sizeshifter: He gains this ability in the epilogue after falling into a vat of toxic waste, and uses it to grow giant to defend Maxville from killer robots.
- Tranquil Fury: As seen when he sees Stitches driving one of his precious buses at the climax.
- Undying Loyalty: It's not explored much, but he seems to have this for the school and, of course, its students.
Gwen's stern widower father and the only parent other than the elder Strongholds to physically appear; he shows he's none too impressed with his daughter's latest flame after Will walks her home from dinner with his parents. He later chaperones at the climactic Homecoming dance. According to Gwen, he's a former Sidekick who retired some time after the death of his wife.
- Chekhov's Gunman: He appears in two brief scenes, once after Will walks Gwen home and again at Homecoming. So he's not exactly the sort of person you'd figure for a supervillain at first glance...
- Four Eyes, Zero Soul: "Zero soul" is a bit much, but he's definitely an imposing fellow whose half-moon spectacles give the impression of looking down on people. The "zero soul" part is later played straight given certain revelations about him.
- Getting Crap Past the Radar: Why do you think a man might be concerned that his teenage daughter's boyfriend has six arms?
- ...Six guns?
- Overprotective Dad: Comes off as overprotective and perhaps even somewhat controlling to his daughter, given that he can get her to leave her boyfriend and come into the house just by jerking his head toward it, and is concerned that said boyfriend might have six arms that he could use to get too handsy.
- Small Role, Big Impact: Ladies and gentlemen, the man responsible for making our villain who she is today.
- The Ugly Guy's Hot Daughter: He's not exactly hideous, but his glasses, dorky sweater-vest, and short height definitely don't lend the impression of someone who could spawn a statuesque knockout like Gwen. And that's because she isn't his biologically.
- Walking Spoiler: Much like his daughter, you can probably tell this guy has a few secrets from those white spaces.
The cloaked mastermind
The films main antagonist, a black-cloaked, bass-voiced mystery malefactor with a serious axe to grind with the Stronghold family. The villain sends a giant robot to attack the city, knowing the Commander will destroy it and take its prominent eyeball for his trophy collection; from there, the mastermind is able to observe the Strongholds Secret Sanctum. It eventually becomes apparent that the masterminds true goal is the Commanders prize possession, a mysterious weapon called the Pacifier acquired on the case that brought Steve and Josie together, which the villain plans on using to exact revenge.
- Attack of the 50-Foot Whatever: Sets a giant robot on the Commander at the beginning of the movie. It was never intended to win, but its eyeball, which the Commander takes home, had a camera in it, enabling the baddies to observe the Strongholds' Secret Sanctum.
- Big Bad: Of the film.
- Black Cloak: Well, obviously. The villain's identity is obscured by it until the climax.
- Collapsible Helmet: Wears a helmet that retracts to hide her identity.
- Comedic Sociopathy: Frequently strangles Stitches when he's being exceptionally aggravating.
- Cool Helmet
- Evil Plan: Steal the Pacifier, turn all the students of Sky High and as many adult heroes as possible into babies with it, and raise them again as supervillains.
- Evil Sounds Deep: An intimidating bass with a mechanical tinge to it, courtesy of Patrick Warburton. This is because she's a teenage girl with a voice scrambler.
- The Faceless: Until the climax, anyway.
- Legacy Character: The mastermind is Gwen Grayson, the second Royal Pain - and the first one reborn.
- Mysterious Watcher: Observes the Strongholds through the camera in the robot eye at first, with the specifics of the evil plan only coming together later on.
- Reincarnation: She's Gwen Grayson, who is Sue Tenny after the Pacifier's energies doubled back on her, reverting her to infancy, after which she was raised until age seventeen by Stitches.
- Revenge: The primary motive of the mastermind and Stitches, revealed to be against Sky High itself for what its Fantastic Caste System did to Sue Tenny.
- Samus Is a Girl: The armor and voice scrambler hide it well, but the mastermind is actually Gwen Grayson.
- Secret Identity Vocal Shift: Speaks with Patrick Warburton's voice, with some slight processing, while the mask is in place.
- Tyke-Bomb: The de-aged Royal Pain was spirited away by Stitches and tutored by him in the ways of evil until she grew up into the lovely Gwen Grayson - and a brand new Royal Pain, the instrument of Sue Tenny's revenge.
- Walking Spoiler: Well, yeah, what do you think the cloak's for?
A sycophantic, jesters bauble-clad supervillain who was a known associate of the late Royal Pain. He vanished after his employers apparent demise, only to reappear seventeen years later in the service of the cloaked mastermind who wishes to steal Royal Pains invention, the Pacifier. Stitches antics frequently aggravate his boss, leading the mastermind to throttle him until he screams the above quote.
- Amazing Technicolor Population: His skin is grey.
- Bald of Evil: He's bald in the modern day while acting as Gwen's father.
- Butt-Monkey: The mastermind subjects him to comedic throttlings quite frequently. He also gets his lights knocked out by an overweight bus driver.
- Catchphrase: See his quote, which he says whenever he gets strangled.
- Co-Dragons: With Penny. He's the actual second-in-command while she's the best fighter.
- Expy: Appears to be a parody of The Fool from King Lear, with his tendency to exclaim "Uncle", talking back to Royal Pain, and possibly acting as Gwen Grayson's dad if the popular "Cordelia is the Fool" theory is to be believed
- The Man in Front of the Man: He is technically the architect of the Evil Plan in the modern day, or possibly acting under failsafe instructions from Sue. He raised Gwen to carry it out but is seemingly content to stay a henchman.
- Mysterious Watcher: Joins his boss is observing the Strongholds.
- Nerd Glasses: Sports a pair as Mr. Grayson.
- Psycho Supporter: A pathetic, evil man who'll do anything his boss asks him.
- Secret Identity: He's Mr. Grayson, Gwen's geeky-looking father.
- Servile Snarker: Has shades of this despite usually being cowed by his boss, at one point trying to get the mastermind to buy him an Xbox.
- Small Role, Big Impact: He's "only" a henchman, but by raising Gwen to carry out Sue Tenny's revenge scheme, he set into motion the entire plot.
- So Proud of You: Villainous variation, as he's positively gleeful at what he's raised his "daughter" to be.
- Super Zeroes: Like Mr. Boy, it's never actually stated what his power is. Probably not much of anything useful, as the powerless Ron Wilson, Bus Driver KOs him with one punch.
- The Svengali: Specifically of the weaker-willed variety that ultimately becomes dependent on their "creation."
- Sycophantic Servant: Up to Eleven. He not only raised his de-aged boss as his own, but rather than take Big Badhood for himself, willingly stepped down to his old henchman position when she came of age.
- Villainous Harlequin: A truly depraved little man who dresses like a jester, though he's definitely not murderous enough to be an out-and-out Monster Clown.
Sue Tenny/Royal Pain
- Played by: Mary Elizabeth Winstead
A high-tech supervillain clad head to toe in powered armor, and notable as the villain whose case brought the worlds favorite super-couple, the Commander and Jetstream, together, seventeen years before the events of the film. Royal Pain invented a mysterious weapon known as the Pacifier, which was damaged by the Commander during their scuffle and exploded, seemingly atomizing the villain. The Pacifier became the Commanders prize possession and the object of the modern-day villains desire.
- Cool Helmet
- Fountain of Youth: The true purpose of the Pacifier: it reverts any person it hits to a newborn baby, primed to be raised as a villain by Royal Pain at her new supervillain academy.
- Freudian Excuse: Her actually very useful power was written off as the stuff of sidekicks in The '70s, and she was placed in the Hero Support track and, it's implied, bullied by the future Commander, later to be known as the world's greatest superhero. Not hard to see why she snapped.
- Heart Is an Awesome Power: Played With. Technopathy is an awesome power in the 2000s with the abundance of computers and sophisticated electronic devices. In The '70s, when technology was a lot more primitive, it wasn't seen as such which is what inspired Sue to begin her scheme.
- Hoist by His Own Petard: Regressed to infancy herself by the Pacifier's energies when it exploded in her arms.
- Hollywood Nerd: Sue's yearbook photo is just Mary Elizabeth Winstead with glasses and no makeup.
- MacGuffin: Royal Pain's invention, the Pacifier, is the story's primary MacGuffin.
- Never Found the Body: Because it was seemingly atomized in the Pacifier explosion. Emphasis on seemingly.
- Powered Armor: Wears a high-tech suit of armor.
- Samus Is a Girl: Under that armor is a very, very angry woman named Sue Tenny.
- Technopath: This is her power, and that of her "daughter" Gwen.
- Unwilling Suspension: Subjects the Commander and All-American Boy to this in the alternate opening.
- Walking Spoiler: You can probably tell from those white spaces this villain is a very important character, despite only being onscreen a few seconds.
- Who's Laughing Now?: Sue Tenny was a bullied outcast at Sky High, so she fled the school and turned to supervillainy to avenge herself of the school's Fantastic Caste System.
- Woobie, Destroyer of Worlds: She got chewed up and spat out by the system, and decided to violently take that system down.
Barron Battle/Baron Battle
An old school rival of Steves from Sky High, who grew up to be one of his greatest enemies and one of the worlds most dangerous supervillains. Steve managed to capture him and he was sentenced to four consecutive life sentences, but not before swearing revenge. He is also Warrens father, and his legacy hangs grimly over his troubled son.
- Arch-Enemy: Was this to the Commander, until he was shipped off to jail.
- The Dreaded: Nothing good and a whole lot of bad is said about this guy.
- Greater-Scope Villain: Said to have been one of the baddest of the bad, dwarfing the current story's villains, and swore he'd have his revenge, but all we see of him in the movie is his yearbook photo.
- Identical Grandson: He apparently looked quite a bit like Warren in his teenage years... though that may be because the photo is Steven Strait with a different hairstyle and glasses.
- Longer-Than-Life Sentence: Four consecutive life sentences, no chance of parole until after his third life.
- Noodle Incident: We never learn precisely what he did to earn those four life sentences.
- Red Herring: Hearing the other characters talk about him one might think he's a good candidate for the identity of the mastermind. He isn't.
- Steven Ulysses Perhero: He just dropped one "r."
- The Unseen: The photo up there is all we get.
- We Will Meet Again: Apparently swore this to the Commander before he was carted off to jail.