History YMMV / SkyHigh2005

* MagnificentBastard: [[spoiler:[[PredecessorVillain Sue Tenney, the original Royal Pain]], is the mastermind of the film's conflict, puppeteering an EvilPlan spanning two decades. [[FromNobodyToNightmare 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 [[SamusIsAGirl 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.]]

** Steve actually considering dropping Will in toxic waste in response to Josie's rhetorical aside wouldn't be funny, but her NotJustNoReaction is.

* MagnificentBitch: [[spoiler:[[PredecessorVillain Sue Tenney, the original Royal Pain]], is the mastermind of the film's conflict, puppeteering an EvilPlan spanning two decades. [[FromNobodyToNightmare 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 [[SamusIsAGirl 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.]]

** Barron Battle has apparently been sentenced to a ''quadruple'' life sentence...with no chance of parole until his '''third.''' (Stacking life sentences, at least, is TruthInTelevision.)

*** That [[spoiler:Gwen]] when approached and given an apology by Will about [[spoiler:[[YouKilledMyFather her "mother" Sue getting "killed"]] years ago]] results in the bombshell reveal that [[spoiler:the two are one in the same]], that [[spoiler: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]].

** 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? 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 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.
** To a lesser extent, [[spoiler: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]].

* CultClassic: A surprisingly strong fanbase for a oneshot production unconnected to any of Disney's better-known properties.

* EvilIsSexy:
** Royal Pain, obviously, especially after it's revealed that [[spoiler:Mary Elizabeth Winstead is playing her]].
** Judging from the number of {{Original Character}}s he gets paired up with, there are plenty of fangirls who have this opinion of [[RubberMan Lash]].
** An in-universe example happens when Coach Boomer is trying to convince Professor Medula to go on a double date. Boomer tells Medula that the girl he's setting him up with is his own date's EvilTwin. Medulla is sold at that.